Lithium n-propyl mercaptide

Finally the methyl ester is cleaved with lithium n-propyl-mercaptide by nucleophilic displacement and the benzyl ether by conventional catalytic hydrogenolysis to furnish (-)-scopadulcic acid (1). [Pg.229]

CLEAVAGE OF ETHERS Aluminum chloride. Boron tribromide. Bromine. Dimethylformamide. Methylmagnesium iodide. Triphenylphosphine dibromide. a-GLYCOLS Silver iododibenzoate KETOXIMES Chromous acetate METHYL ESTERS Lithium n-propyl mercaptide. [Pg.178]

An improved reagent for the G-alkyl cleavage of methyl esters by nucleophilic displacement has been found by a Stanford group lithium n-propyl mercaptide (from n-butyl-lithium and n-propyl mercaptan) in hexa-methylphosphoramide smoothly and selectively cleaves methyl esters to the corresponding carboxylic acid salts. The use of boron trichloride in dichloro-methane is recommended for the cleavage of sterically hindered methyl esters methyl ethers are unaffected. [Pg.103]