Ammonium Chloride → HCID 86749280, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl (E) 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-3-(3-bromopropyl)-4-methylhex-4-enoate (420 mg) was cooled to -78° C. in THF (50 ml), and a 1M solution of sodium bis (trimethylsilyl) amide (1.88 ml) in THF was added slowly. The reaction was stirred for 45 min at -78° C., and then allowed to warm to 0° C. over 15 minutes, at which time 5 ml of 1N NH4Cl) was added. The THF was evaporated, the aqueous layer extracted with ether, the ether layer washed with 1N HCl, brine, and then dried. Evaporation of the solvent gave an oil, which was chromatographed on silica gel (20%-25% ethyl acetate in hexanes) to give ethyl (E) 2-[-3-(4-hydroxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-1-methylpropenyl]-cyclopentanecarboxylate (235 mg), a compound of Formula I-ZH-A1, as an oil.

Provenance & Evidence