Hydrochloric Acid → HCID 68776274, compound

Participants

Reaction Steps

At 5° C., a solution of 7-methylspiro[4.5]dec-9-ene-6-carboxylic acid (1.4 g, 7.2 mmol) in DMF was treated with K2CO3 (1.1 g, 7.9 mmol). The resulting mixture was stirred for 30 min., treated with methyl iodide (0.67 ml, 10.8 mmol), stirred at 20° C. for 2 h, poured into cold 2N aqueous HCl (20 ml), and extracted twice with hexane (70 ml). The combined organic phases were washed with water (50 ml), with a saturated aqueous solution of NaCl (50 ml), dried (MgSO4), and concentrated. FC (170 g SiO2, pentane/diethyl ether 80:1) of the crude product (1.4 g) gave rel-(6R,7S)-methyl 7-methylspiro[4.5]dec-9-ene-6-carboxylate (0.15 g, 10%) and rel-(6S,7S)-methyl 7-methylspiro[4.5]dec-9-ene-6-carboxylate (0.53 g, 35%).

Provenance & Evidence