Ammonium Chloride → HCID 68833946, compound

Participants

Reaction Steps

Lithium bis(trimethylsilyl)amide (1.06 M in THF; 12.6 mL, 13.3 mmol) was added dropwise over 10 min to a stirred solution of benzyl (4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)acetate (4.32 g, 12.1 mmol) in THF (40 mL) at −78° C. under nitrogen. On completion of addition stirring was continued at −78° C. for 30 min then t-butylbromoacteate (2.82 g, 2.14 mL, 14.5 mmol) was added dropwise over 5 min. The reaction was allowed to warm slowly to room temperature over 4 h then saturated ammonium chloride solution (40 mL) was added and the resulting suspension extracted with ethyl acetate (3×50 mL). The organic phases were combined, dried (magnesium sulfate) and evaporated to dryness. The residue was chromatographed on silica gel (5% diethyl ether: cyclohexane) to give the title compound as a colourless oil (5.35 g, 94%). LC/MS: 4.35 min; z/e 488, calcd (M+18) 488. 1H NMR (400 MHz: CDCl3): 7.10 (3H), 7.05 (2H), 6.95 (2H), 6.60 (2H), 4.95 (2H), 3.85 (1H), 2.90 (1H), 2.40 (1H) 1.20 (9H), 0.8 (9H), 0.05 (6H).

Provenance & Evidence