Lithium diisopropylamide → HCID 42614041, compound

Participants

Reaction Steps

To a stirred solution of 44 (1.528 g, 4 mmol) in tetrahydrofuran (40 ml) was added dropwise lithium diisopropylamide in tetrahydrofuran (2.0 M) (8 ml, 16 mmol) under an atmosphere of Argon at room temperature. The reaction mixture was stirred for 0.5 hour at room temperature, after which it was quenched by addition of dropwise water (0.5 ml). The solvents were evaporated under reduced pressure, and the residue was purified by flash chromatography on silica gel (2:1-0:1 v/v hexanes/CH2Cl2) to give the product as white solid (0.503 g, 57%). 1H NMR (300 MHz, CDCl3): δ 7.67 (1H, aromatics), 7.37-7.18 (7H, aromatics), 4.5 (1H, dd, J=2.1, 14.7 Hz, CHOH), 3.0 (1H, dd, J=2.1, 14.7 Hz, CH), 2.8 (1H, dd, J=2.1, 14.7 Hz, CH2). 13C NMR (75 MHz, CDCl3): δ 154.5, 150.6, 128.6, 127.1, 1127.0, 126.0, 125.8, 125.1, 124.7, 123.0, 122.7, 121.7, 111.9, 109.6, 74.2, 47.7.

Provenance & Evidence