Sodium Hydroxide → HCID 66685725, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (1-(4-chlorophenyl)cyclobutyl)methanol (1.5 g, 7.63 mmol) in toluene (21 mL) was cooled to 0° C. and treated with a 33% aq. NaOH solution (7.43 mL) followed by tetrabutylammonium hydrogen sulfate (647 mg, 1.91 mmol). The mixture was stirred at 0° C. for 10 min and tert-butyl bromoacetate (1.11 mL, 7.63 mmol) was added. The ice bath was removed, and stirring was continued at room temperature for 50 min. Additional tert-butyl bromoacetate (1.11 mL, 7.63 mmol) was added and the mixture was stirred at room temperature for 16 h. Additional tert-butyl bromoacetate (1.11 mL, 7.63 mmol) was added and the mixture was stirred at room temperature for additional 24 h. The reaction mixture was diluted with EtOAc and water. The organic layer was separated, washed with water, brine, dried (Na2SO4), and concentrated. The crude oil was chromatographed on silica gel (Teledyne-Isco RediSep 80 g silica gel column) and eluted with hexanes, followed by 1% and 2% EtOAc in hexanes to obtain tert-butyl 2-((1-(4-chlorophenyl)cyclobutyl)methoxy)acetate (1.77 g, 75% yield) as a white solid. 1H NMR (400 MHz, CDCl3): δ ppm 7.25-7.28 (2 H, m), 7.06-7.19 (2 H, m), 3.85 (2 H, s), 3.64 (2 H, s), 2.22-2.49 (4 H, m), 1.98-2.18 (1 H, m), 1.73-1.93 (1 H, m), 1.45 (9 H, s).

Provenance & Evidence