Lithium Bromide-Assisted Protection of Primary and Secondary Alcohols as Methoxymethyl Ethers using Dimethoxymethane

Synthesis of deuterated fatty acids to investigate the biosynthetic pathway of disparlure, the sex pheromone of the Gypsy Moth, Lymantria dispar

“…This compound was prepared following the procedure reported by Gras et al (7). To a stirred solution of bromoalcohol 1 (3.98 g, 15 mmol) in 60 mL of dimethoxymethane (DMM) were added LiBr (435 mg, 5 mmol) and p-toluenesulfonic acid (p-TSOH; 190 mg, 1 mmol) at room temperature, and stirring was continued overnight.…”

“…Methyl-1-heptanol(7). Product 6 (1.13 g, 3 mmol) was trityl-deprotected to the corresponding alcohol by treatment with 60 mL of a MeOH/CHCl 2 COOH solution (6%) for 48 h at room temperature.…”

Synthesis of 1,3,4,5‐Tetrahydro‐2‐benzoxepin Derivatives as Conformationally Restricted Analogues of cyclamenaldehyde‐type compounds and as intermediates for highly odour‐active homologues

“…-The synthesis of the 1,3,4,5-tetrahydro-2-benzoxepin derivative 10a started from alcohol 8a. Rieche and Gross [I91 have shown that tetrahydro-2-benzoxepins can be directly obtained from 3-phenylpropanols by cyclization of intermediate chloromethyl ethers in the presence of AICl, in CS,; in analogy to the synthesis of isochromans 1201, we found it more convenient to work via the intermediate methoxymethyl ether 9a, prepared by using a published procedure [21]. Indeed, 9a was smoothly cyclized to the desired product 10a in the presence of AlC1, in CH,Cl, (see Scheme 1).…”

“…The mixture was allowed to reach r.t., Na2S04 was added and the mixture filtered and evaporated (14 g). Bulb-to-bulb distillation (0.1 mbar, oven temp.+130°) gave l l c (purity 95%; 12.5 g, 97% [21]). To a soln.…”

Enantioselective Total Synthesis of (+)‐Homochelidonine by a PdII‐Catalyzed Asymmetric Ring‐Opening Reaction of a meso‐Azabicyclic Alkene with an Aryl Boronic Acid

“…The hydroxy group was then protected as the MOM ether in 71 % yield by stirring 15 in dimethoxymethane at RT in the presence of a catalytic amount of LiBr and p-toluenesulfonic acid. [11] Aryl bromide 16 was converted into the corresponding boronic acid 17 in 63 % yield by lithium-halogen exchange with nBuLi and subsequent quenching with triisopropyl borate.…”