Trimethylamine → 4-(((tert-Butyl(dimethyl)silyl)oxy)methyl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of oxalyichloride (1.6 ml) in dry dichloromethane (37 ml) was cooled to -70° C. under N2. Dry dimethylsulfoxide (2.5 ml) in dichloromethane (10 ml) and a solution of 4-(tert-butyldimethylsilyloxymethyl)benzylalcohol (24) (3.94 g, 15.6 mmol) in dichloromethane (20 ml) were added carefully. The reaction mixture was stirred at -70° C. for 1 h. trimethylamine (12 ml) was then added. The reaction mixture was allowed to warm up no 0° C. Saturated aqueous sodium bicarbonate (50 ml) was added, the organic layer was separated and the aqueous layer was extracted with dichloromethane (4×50 ml). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography over silica (dichloromethane/hexane; 4:1) to yield 4-butyldimethylsilyloxymethyl)benzaldehyde (25) 3.21 g, 82%); νmax /cm-1 2020s, 2850s, 2730w, 1700s, 1090s; δH (CDCl3) 0.11 (6H, s, SiCH3), 0.94 (9 H, s, tert-butyl), 4.80 (2 H, s, CH2O), 7.47 and 7.84 (4 H, AA'BB', PhH) and 9.98 (1 H, s, CHO); (CDCl3) -5.3, 18.4, 25.9, 64.4, 126.2, 129.8, 135.3, 148.6 and 192.0; m/z 251.1467 M+ +H).

Provenance & Evidence