Diisobutylaluminum hydride → HCID 178496545, compound
Reaction equation
[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]2[CH:18]=[CH:17][C:12]([C:13](OC)=[O:14])=[C:11]([CH3:19])[CH:10]=2)[CH2:5][CH2:4]1.CC(C[AlH]CC(C)C)C>C1COCC1>[CH3:1][O:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]2[CH:18]=[CH:17][C:12]([CH2:13][OH:14])=[C:11]([CH3:19])[CH:10]=2)[CH2:7][CH2:8]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a cooled (−78° C.) solution of the title compound from Example 13 Step F (90.0 mg, 0.343 mmol) in THF (1.7 mL) was added DIBAL-H (1.03 mL, 1.0 M in toluene, 1.03 mmol). After 30 min, the reaction mixture was allowed to warm to 0° C. After 2 h, the reaction mixture was quenched by addition of MeOH (0.140 mL). The resulting mixture was diluted with diethyl ether and saturated aqueous sodium/potassium tartrate, and the mixture was stirred rapidly until a clear phase separation was achieved. The organic phase was then separated, dried over anhydrous sodium sulfate, and concentrated in vacuo to provide the title compound, which was used without further purification.
Workup
- waitAfter 2 h
- customthe reaction mixture was quenched by addition of MeOH (0.140 mL)
- additionThe resulting mixture was diluted with diethyl ether and saturated aqueous sodium/potassium tartrate
- customThe organic phase was then separated
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-20edbe71fcea4e378d21261ca28d2c2a
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08455638B2
Reaction notes
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