Ammonium Chloride → HCID 69927504, compound

Participants

Reaction Steps

279 mg (0.69 mmol) of (2S,3S,4R)-2-(cyclohex-1-enyl)-3-methoxy-4-p-methoxybenzyloxyhex-5-enoic acid methoxymethylamide are dissolved in THF (4 mL) and treated, at 0° C., with an excess of vinylmagnesium bromide (as a 1M solution in THF, 2.76 mL, 2.76 mmol, 4 equivalents). After addition, the mixture is allowed to warm to room temperature and is stirred overnight. An excess of saturated NH4Cl in a 1:1 THF/water mixture is then added. After extraction and evaporation of the solvents, the residue is chromatographed on silica (eluent (5/1 Cy/EtOAc)) to give 187 mg (73%) of (4S,5S,6R)-4-(cyclohex-1-enyl)-5-methoxy-6-p-methoxybenzyloxyocta-1,7-dien-3-one.

Provenance & Evidence