Sodium Hydroxide → HCID 68744497, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of NaOH (100 mg, 2.5 mmol), n-Bu4NI (37 mg, 0.1 mmol), 3-(hexyloxy)phenyl benzoate (ref. Prasad K. et al. Org. Proc. Res. Dev., 2003, 7 (5), 743-749) (200 mg, 0.67 mmol) in H2O (3 mL) was evacuated and refilled with Ar three times. The reaction mix was heated with stirring to 90° C. under Ar and treated with 5-bromo-1,1-dimethoxypentane (0.24 g, 1.2 mmol), added dropwise over 30 min at 95° C. Stirring was continued at 95° C. overnight. Later, the reaction mixture was cooled to rt and extracted with Et2O (2×). The organic extracts were washed (2 M aq NaOH, brine), concentrated under reduced pressure and purified by flash chromatography on silica gel using 0-7% EtOAc/hexanes as the eluent to afford the title compound as a colorless oil (127 mg, 59%). 1H NMR (400 MHz, CDCl3) δ ppm 7.15 (t, J=8.08 Hz, 1 H), 6.43-6.52 (m, 3 H), 4.89 (t, J=4.67 Hz, 1 H), 3.82-4.03 (m, 10 H), 1.20-1.92 (m, 14 H), 0.91 (t, J=6.82 Hz, 3 H).

Provenance & Evidence