Trimethylsilyldiazomethane → HCID 20638810, compound

Participants

Reaction Steps

To a solution of 900 mg (4.45 mmol) of 1(R)-phenyl-2(S)-carboxy cyclohex-5-ene (See U.S. Pat. No. 5,750,549, Example 158, Step B) in a 4:1 solution of MeOH/THF was added trimethylsilyldiazomethane until a yellow color persisted. After stirring at room temperature for 3 hour the reaction was concentrated in vacuo and the residue was purified by flash chromatography eluting with 0-15% EtOAc in hexanes to afford the ester (300 mg) as a colorless oil. 1H NMR (CDCl3, 500 MHz) δ 7.19-7.30 (m, 5H), 5.98-6.01 (m, 1H), 5.76-5.79 (m, 1H),3.89 (s, 1H),3.50 (s, 3H), 2.95-2.98 (m, 1H), 2.16-2.32 (m, 2H),1.80-1.87 (m, 2H) ppm.

Provenance & Evidence