Ammonium Chloride → methyl (4RS,6SR)-6-(3,4-dichlorophenyl)-6-hydroxy-2,4,-dimethylcyclohex-1-enecarboxylate

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Reaction Steps

A solution of racemic methyl 2,4-dimethyl-6-oxocyclohex-1-enecarboxylate (Example 1-03, Step 4; 100 mg) in THF (5 mL) was treated with 3,4-dichlorophenylmagnesium bromide (0.5 M, 1.3 mL). The mixture was stirred at rt overnight and then treated with saturated aqueous ammonium chloride. The resulting mixture was extracted three times with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under vacuum to provide methyl (4RS,6SR)-6-(3,4-dichlorophenyl)-6-hydroxy-2,4,-dimethylcyclohex-1-enecarboxylate (97 mg). Mass spectrum m/z 353.32 (M+Na+).

Provenance & Evidence