Isobutyraldehyde → HCID 59784097, compound

Participants

Reaction Steps

Intermediate 7 (250 mg, 0.46 mmol) is dissolved in 1,2-dichloroethane (4 mL), to which is added iso-butyraldehyde (63 μL, 0.69 mmol) and NaBH(OAc)3 (146 mg, 0.69 mmol). This mixture is stirred under N2 at RT overnight. LCMS at this point shows a small amount of unreacted starting material so further quantities of iso-butyraldehyde (63 μL, 0.69 mmol) and NaBH(OAc)3 (146 mg, 0.69 mmol) are added. After a further 4 h. of stirring at RT the reaction mixture is diluted with CH2Cl2 (50 mL) and then washed with water (50 mL), brine (50 mL) and dried (Na2SO4). After filtration, the solvent is removed under reduced pressure to afford an oil which is purified by flash chromatography on silica gel (10-50% Et2O/CH2Cl2). The title compound is isolated as a white foam (255 mg, 92% yield): 1H NMR δ (CDCl3) 6.72-7.27 (m, 5H), 4.37-5.24 br m, 5H), 3.26-3.90 (br m, 2H), 2.67-2.96 (br m, 6H), 1.62-2.19 (m, 1H), 1.48 (s, 9H), 1.23-1.34 (m, 3H), 0.69-0.99 (m, 12H); LCMS (APCl+) 601.3 (MH+, 100%).

Provenance & Evidence