Water → HCID 53725716, compound

HRID 1297025Notes

Reaction equation

HRID 1297025 reaction equation
[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][CH:9]=[CH:10][C:11](OCC)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.O>ClCCl>[C:16]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH:9]=[CH:10][CH2:11][OH:12])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 69429952HCID 69429952, compound

Product 1

HCID 53725716HCID 53725716, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.22 mg (7.92 mmol) of ethyl 5,5-diphenyl-2-pentenoate was dissolved in 30 ml of dichloromethane. 16.1 ml (15.1 mmol) of diisobutylaluminum hydride (0.94 mol/L: hexane solution) was added to the obtained solution under cooling with ice, and they were stirred at room temperature for 2 days. Water was added to the reaction mixture and they were stirred under cooling with ice. The precipitate thus formed was filtered through Celite. The precipitate was washed with ethyl acetate. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by the silica gel chromatography (hexane/ethyl acetate=3/1 to 1/1) to obtain the title compound.

Workup

  1. temperatureunder cooling with ice, and they
  2. stirringwere stirred
  3. temperatureunder cooling with ice
  4. customThe precipitate thus formed
  5. filtrationwas filtered through Celite
  6. washThe precipitate was washed with ethyl acetate
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe obtained residue was purified by the silica gel chromatography (hexane/ethyl acetate=3/1 to 1/1)

Sources & evidence

ORD record
ord-fd4d18eab9ef4493ac796f98975d0721
Source dataset
uspto-grants-2007_07
Patent number
US07247645B2

Reaction notes

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