Diisobutylaluminumhydride → HCID 22491013, compound
Reaction equation
[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:22][CH3:23])=[C:10](/[C:13](/[CH3:21])=[C:14](/[F:20])\[C:15](OCC)=[O:16])[CH:11]=2)[O:6][C:5]([CH3:25])([CH3:24])[CH:4]=1)[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:22][CH3:23])=[C:10](/[C:13](/[CH3:21])=[C:14](/[F:20])\[CH2:15][OH:16])[CH:11]=2)[O:6][C:5]([CH3:24])([CH3:25])[CH:4]=1)[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of ethyl (2E)-3-(4-ethyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-2-fluoro-but-2-enoate (Compound 68, 349 mg, 0.96 mmol) in THF (15 mL) under argon at 0° C. was added diisobutylaluminum hydride (1.0 M in hexanes, 2.9 mL, 2.9 mmol). The resulting mixture was stirred at −78° C. for 4 h. The reaction was quenched slowly with saturated NH4Cl, celite, and diluted with diethyl ether. The resulting mixture was stirred at 25° C. for 1 h. The product was filtered through a pad of celite. The solution was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 1:4 ethyl acetate/hexane) to yield the title compound as a yellow solid.
Workup
- customThe reaction was quenched slowly with saturated NH4Cl, celite
- additiondiluted with diethyl ether
- stirringThe resulting mixture was stirred at 25° C. for 1 h
- filtrationThe product was filtered through a pad of celite
- dry with materialThe solution was dried over Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by flash column chromatography (silica gel, 1:4 ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-9a475d3c86674d41aac8f79b0fd16d97
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06887896B1
Reaction notes
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