Diethyl Ether → HCID 68524880, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 3,4-dihydro-1,5-benzoxazepine-5(2H)-carboxylate (2.15 g, 8.62 mmol) in 50 mL of diethyl ether at −78° C. was added N,N,N′,N′-tetramethylethylenediamine (1.6 mL, 10.35 mmol) and then sec-butyllithium (8.0 mL of a 1.3 M solution in cyclohexane, 10.35 mmol) was added dropwise via addition funnel. The mixture was stirred at −78° C. for 1 h and then N,N-dimethylformamide (1.0 mL, 12.93 mmol) was added dropwise in 10 mL of diethyl ether and the resulting mixture was stirred at −78° C. for 1 h. The reaction was quenched by the addition of 10 mL of saturated aqueous ammonium chloride and then was diluted with water and ethyl acetate. The organics were washed with 10% aqueous HCl, sat'd aq. sodium bicarbonate and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (elution with 5:1 hexane/ethyl acetate) to afford 2.0 g (84%) of the title compound as an oil which was determined to be a mixture of the title compound and the 9-formyl regioisomer. The mixture of products was carried forward.

Provenance & Evidence