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

HRID 1647544Notes

Reaction equation

[CH2:1]([O:8][CH:9]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:10][C:11](OCC)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>CCOCC>[CH2:1]([O:8][CH:9]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:10][CH:11]=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

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##

Workup

customby quench with methanol (20 mL)
temperatureto warm to 0° C.
washwashed 2 times with potassium sodium tartrate, tetrahydrate 20% solution in water (2@250 mL)
dry with materialbrine (200 mL) and then dried over anhydrous magnesium sulfate
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-c15d42f8621b49578f33253c43a83a2e
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05432273

Reaction notes

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