Diisobutylaluminum hydride → 3-(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)propan-1-ol
Reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][CH2:23][CH:24]=[O:25])([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][CH2:23][CH2:24][OH:25])([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 3-(1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)propanal (40 mg, 0.119 mmol) in DCM (1 mL) at −78° C. under N2 was added 1M DIBAL-H in DCM (0.178 ml, 0.178 mmol). The reaction mixture was stirred at −78° C. for 2 h and then added CELITE® (250 mg). The reaction was quenched with sat′d aqueous NH4Cl (0.5 mL) at −78° C. and then stirred at rt for 30 min. MgSO4 (200 mg) was added and the mixture was stirred at rt for 1 h. The mixture was filtered. The solid was washed with DCM. The combined filtrates were concentrated in vacuo to afford the title compound (40 mg, 99% yield) as an oil. LCMS, [M+NH4]+=356.2.
Workup
- additionadded CELITE® (250 mg)
- customThe reaction was quenched with sat′d aqueous NH4Cl (0.5 mL) at −78° C.
- stirringstirred at rt for 30 min
- additionMgSO4 (200 mg) was added
- stirringthe mixture was stirred at rt for 1 h
- filtrationThe mixture was filtered
- washThe solid was washed with DCM
- concentrationThe combined filtrates were concentrated in vacuo
Sources & evidence
- ORD record
- ord-ffa7235b6436425f8c74b579e6cdb7a7
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962660B2
Reaction notes
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