Hydrochloric Acid → HCID 18663597, compound

Participants

Reaction Conditions

Reaction Steps

2.0 ml (18.33 mmol) of N-methylmorpholine and 2.4 ml (18.33 mmol) of isobutyl chloroformate are added dropwise at -15° C. to a solution of 5.0 g (18.33 mmol) of 1-chloro-dibenz[b,f]oxepine-10-carboxylic acid in dimethoxyethane. After 5 minutes filtration is carried out and at -15° C. a solution of 1.39 g (36.67 mmol) of sodium borohydride in 15 ml of water is added dropwise to the filtrate. The mixture is stirred for 15 minutes at -15° C., then 35 ml of 1N hydrochloric acid are added and the mixture is allowed to warm to room temperature. The reaction mixture is rendered basic with sodium hydroxide and extracted 4× with ethyl acetate. The organic phase is washed 1× with water, dried over sodium sulfate and concentrated. 4.58 g (17.7 mmol)=96.6% of crude (1-chlorodibenz[b,f]oxepin-10-yl)-methanol are obtained in the form of a yellow oil; TLC (silica gel; ethyl acetate/hexane=1:1; UV): Rf =10.46; 1H-NMR (CDCl3, 200 MHz): 2.42 (sbr, 1H); 1H); 4.71 (s, 2H); 7.10-7.45 (m, 7H).

Provenance & Evidence