Methanol → HCID 45139978, compound

Participants

Reaction Conditions

Reaction Steps

Compound 38a (3.21 g, 9.70 mmol) was dissolved in 120 ml of CH2Cl2 and cooled to −78° C. 1M boron tribromide (30 ml) was added dropwise and the mixture was allowed to warm to ambient temperature and was stirred overnight. Sat. NaHCO3 was added and the product extracted with dichloromethane, dried (Na2SO4), filtered, and concentrated to yield the crude product. Column chromatography (7:3:1 CH2Cl2:MeOH:Et3N) afforded 2.41 g (84%) of 39a. 1H NMR (400 MHz, CDCl3) 0.98-1.02 (t, 3H, 7.6 Hz), 1.27-1.31 (m, 2H), 1.70-1.82 (m, 3H), 2.25-2.28 (m, 1H), 2.58-2.06 (m, 1H), 2.73-2.78 (m, 4H), 2.97-3.09 (m, 5H), 3.16-3.20 (m, 9H), 6.45 (s, 1H), 6.53-6.55 (d, 1H, J=9.2 Hz), 6.84-6.85 (d, 1H, J=8.4 Hz).

Provenance & Evidence