A Convenient Method for the Conversion of Halides to Alcohols

Alexander, Jose; Renyer, Mara L.; Veerapanane, H.

doi:10.1080/00397919508011463

Cited by 22 publications

(17 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[17] With 1 mol% Ir[dF(CF 3 )ppy] 2 (dtbbpy)PF 6 as catalyst under irradiation of blule LEDs for 1.5 h, Z-3a could be achieved in excellent yield with Z/E ratio of 99∶1 observed on GC. Electron-affacting groups in Z-3b and Z-3c did not impact this conversion of E-Z configuration, and corresponding Z-3b and Z-3c could be isolated in 95% and 96% yields, respectively.…”

Section: Resultsmentioning

confidence: 97%

“…The solution was stirred for 2 h and then diluted with EtOAc, The mixture was cautiously washed with NaHCO 3 solution, H 2 O and brine, dried with anhydrous Na 2 SO 4 , and concentrated. The residue was purified by chromatography on silica gel (petroleumether/EtOAc, V∶V＝4∶1) to provide the desired product 5 [17] 6, 136.1, 133.0, 131.3, 130.1, 113.5, 98.7, 62.7, 62.2, 55.2, 32.6;IR (film) ν: 3362, 2955IR (film) ν: 3362, , 2933IR (film) ν: 3362, , 2837IR (film) ν: 3362, , 1609IR (film) ν: 3362, , 1512IR (film) ν: 3362, , 1247IR (film) ν: 3362, , 1177IR (film) ν: 3362, , 1034 …”

Section: Synthesis Of Compoundmentioning

confidence: 99%

See 1 more Smart Citation

E-Z Isomerization of 1, 5-Bromotrichloromethylation Reaction Products and Trisubstituted Styrenes

李进¹,

陈靖之²,

黄文浩³

et al. 2018

Chin. J. Org. Chem.

View full text Add to dashboard Cite

Section: Resultsmentioning

confidence: 97%

Section: Synthesis Of Compoundmentioning

confidence: 99%

E-Z Isomerization of 1, 5-Bromotrichloromethylation Reaction Products and Trisubstituted Styrenes

李进¹,

陈靖之²,

黄文浩³

et al. 2018

Chin. J. Org. Chem.

View full text Add to dashboard Cite

“…Chlorosulfonation and treatment of the isoxazoline 57 with sulfonyl chloride with aqueous ammonia afforded the sulfonamide derivative 58 . Final treatment of sulfonamide derivative with formic acid in presence of triethylamine followed by hydrolysis with aqueous NaOH 53 furnished the hydroxymethyl analogue of valdecoxib 59 (Scheme 17). 38 …”

Section: 3 Condensation Reactionsmentioning

confidence: 99%

Recent methodologies toward the synthesis of valdecoxib: A potential 3,4-diarylisoxazolyl COX-II inhibitor

Dadiboyena

Nefzi

2010

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

Non-steroidal anti-inflammatory drugs are widely used therapeutic agents in the treatment of inflammation, pain and fever. Cyclooxygenase catalyzes the initial step of biotransformation of arachidonic acid to prostanoids, and exist as three distinct isozymes; COX-I, COX-II and COX-III. Selective COX-II inhibitors are a class of potential anti-inflammatory, analgesic, and antipyretic drugs with reduced gastrointestinal (GI) side effects compared to nonselective inhibitors. 3,4-diarylisoxazole scaffold is recurrently found in a wide variety of NSAIDs, protein kinase inhibitors, hypertensive agents, and estrogen receptor (ER) modulators. In the present review, we document on the recent synthetic strategies of 3,4-diarylisoxazolyl scaffolds of valdecoxib and its relevant structural analogues.

show abstract

“…The success of the existing methods which include alkaline and metal-mediated hydrolysis is largely dependent on the halocompound used [16][17][18] . Nevertheless, 1-phenylethyl bromide and methyl 2-bromopropionate were refluxed with calcium carbonate in a mixture of water and 1,4-dioxane, and the products were extracted with methylene chloride.…”

Section: Conversion Of An Alkyl Halide Into An Alcohol Solvolysismentioning

confidence: 99%

Synthesis of polymers with hydroxyl end groups by atom transfer radical polymerization

Coessens¹,

Matyjaszewski²

1999

Macromol. Rapid Commun.

View full text Add to dashboard Cite

SUMMARY: Polymers prepared by atom transfer radical polymerization (ATRP) contain end groups defined by the initiator used. Alkyl halides, used as initiators, lead to polymers with an alkyl group at one end and a halide as the other chain end. Using functionalized initiators such as 2-hydroxyethyl 2-bromopropionate, hydroxyl groups can be directly incorporated at one polymer chain end while the other end functionality remains a halogen. The direct displacement of the halogen end groups with hydroxyl groups was unsuccessful due to side reactions such as elimination (for polystyrene) or hydrolysis of ester functions (for polyacrylate). Another approach to generate hydroxyl end groups was based on the substitution of the halogen end groups by ethanolamine. This was successful for polystyrene but additional substitution at the backbone esters was observed in polyacrylates. Multiple substitution reactions could be avoided by using 4-aminobutanol instead of 2-aminoethanol. Hydroxyl terminated polyacrylates were also obtained by extending the polyacrylate chain end with one allyl alcohol unit in a one-pot process by adding an excess of allyl alcohol at the end of e polymerization of acrylate.

show abstract

A Convenient Method for the Conversion of Halides to Alcohols

Cited by 22 publications

References 9 publications

E-Z Isomerization of 1, 5-Bromotrichloromethylation Reaction Products and Trisubstituted Styrenes

E-Z Isomerization of 1, 5-Bromotrichloromethylation Reaction Products and Trisubstituted Styrenes

Recent methodologies toward the synthesis of valdecoxib: A potential 3,4-diarylisoxazolyl COX-II inhibitor

Synthesis of polymers with hydroxyl end groups by atom transfer radical polymerization

Contact Info

Product

Resources

About