Sodium Hydroxide → HCID 45139977, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of LiAlH4 (1.735 g, 45.73 mmol) in THF (100 ml) at 0° C. was added 7a (3.16 g, 9.15 mmol) in a solution of THF (25 ml). After addition, the mixture was refluxed for 2 h and cooled to 0° C. 15% NaOH was added dropwise to quench the reaction and deactivate the LiAlH4, and the mixture stirred for 20 min, and filtered, washed with ethyl acetate. The solution was dried over Na2SO4, filtered, and concentrated. This crude product was then purified through column chromatography using 20% MeOH in ethyl acetate to get 8a as transparent thick liquid (2.23 g, 74%). 1H NMR (400 MHz, CDCl3) δ ppm 0.91-0.96 (t, 3H, J=10 Hz), 1.40-1.6 (m, 3H), 1.97-2.01 (m, 1H), 2.139 (bs, 1H) 2.41-3.11 (m, 18H), 3.82 (s, 3H), 6.61 (s, 1H), 6.66-6.79 (d, 1H, J=6 Hz), 6.95-6.98 (d, 1H, J=8.8 Hz).

Provenance & Evidence