Ethyl 3,3-dibenzyloxypropionate → 3,3-Dibenzyloxypropanal

Participants

Reaction Conditions

Reaction Steps

To a 1000 mL round-bottomed flask was added ethyl 3,3-dibenzyloxypropionate (9, 15 g, 0.0477 mole) and ether (300 mL). The solution was cooled to -78° C. under a dry argon atmosphere and diisobutylaluminum hydride (47.7 mL of 1M solution in hexanes, 0.0477 mole) was added dropwise. The mixture was stirred for 0.5 h at -78° C. followed by quench with methanol (20 mL). The mixture was allowed to warm to 0° C. and washed 2 times with potassium sodium tartrate, tetrahydrate 20% solution in water (2@250 mL), brine (200 mL) and then dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give 3,3-dibenzyloxypropanal as a colorless oil (12.1 g, 94% yield): 1H NMR d 2.83 (dd, 2H, J=2, 5.3 Hz), 4.61 (d, 2H, J =11.6 Hz), 4.69 (d, 2H, J=11.6 Hz), 5.20 (t, 1H, J=5.5 Hz), 7.27-7.36 (m, 10H), 9.74 (s, 1H); IR (Neat) 3100, 3080, 3045, 2940, 2895, 1735, 1500, 1460, 1390, 1360, 1210, 1110, 1060, 1030, 740, 700. ##STR11##

Provenance & Evidence