Ethyl Acetate → HCID 11507368, compound

Participants

Reaction Steps

To a solution of 5,7-diethyl-6-hydroxyspiro[chroman-2,1′-cyclobutane]-8-carbaldehyde (160 mg) prepared as described herein, in methanol (10 mL) was added excess of sodium borohydride and stirred at room temperature for 2 hours. Work up and chromatography (silica gel, ethyl acetate in hexane 5% to 15%) gave 130 mg of product. 1H-NMR (300 MHz, CDCl3) δ=4.80-4.70 (m, 3H), 2.85-2.55 (m, 7H), 2.30-1.60 (m, 8H), 1.20-1.10 (m, 6H) ppm. 13C-NMR (75 MHz, CDCl3) δ=146.3, 144.7, 128.2, 127.8, 124.7, 118.1, 76.9, 58.0, 34.2, 29.3, 19.6, 15.3, 13.4, 12.6 ppm. MS (m/z)=259 (100, M−OH)+.

Provenance & Evidence