Potassium Hydroxide → HCID 68722407, compound

Participants

Reaction Steps

A solution of KOH (19.1 g, 289 mmol) in ethanol (60 ml) was treated with rel-(6S,7S)-ethyl 7-methylspiro[4.5]dec-9-ene-6-carboxylate (4.28 g, 19.2 mmol, prepared as described in Example 19) and after refluxing for 3 d, the resulting mixture was poured into cold 2N aqueous NaOH (100 ml), and extracted twice with cyclohexane (50 ml). The combined aqueous phases were acidified with conc. HCl, extracted twice with MTBE (50 ml), and the combined org. phases were washed with water (50 ml), with a saturated aqueous solution of NaCl (50 ml), dried (MgSO4), and concentrated. FC (300 g SiO2, hexane/MTBE 8:1) of the crude product (2.65 g) gave 7-methylspiro[4.5]dec-9-ene-6-carboxylic acid (1.4 g, 37%).

Provenance & Evidence