Dichloromethane → HCID 86587083, compound

Participants

Reaction Conditions

Reaction Steps

CH2Cl2 (0.80 mL, 12.7 mmol) was added to THF (40 mL) and cooled to −100° C. n-BuLi (1.6 N, 6.3 mL) was slowly added while maintaining a temperature of −100° C. The flask was stirred at −100° C. for an additional 45 min. Pinanediol (1-benzyloxyethyl)boronate (2.66 g, 8.46 mmol), dissolved in THF (20 mL), was added followed by a solution of zinc(II) chloride in ether (1.0 N, 17 mL). The THF was evaporated and the residue was redissolved in hexanes (150 mL). The solution was washed with saturated aqueous ammonium chloride, brine, and dried over MgSO4. It was concentrated to give a light oil. This oil was purified by silica gel column chromatography (10% ethyl acetate/90% hexanes eluant) to yield 1.55 g (51%) of a clear oil. 1H-NMR (CDCl3)δ 7.36 (m, 5H), 4.58 (m, 2H), 4.37 (d, 1H), 3.91 (m, 1H), 3.56 (d, 2H), 2.39-1.81 (m, 6H), 1.40 (d, 3H), 1.34 (d, 3H), 1.29 (s, 3H), 0.84 (s, 3H).

Provenance & Evidence