Diisobutylaluminumhydride → HCID 59882242, compound

HRID 1835030Notes

Reaction equation

HRID 1835030 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH:13]2[CH2:15][CH2:14]2)[C:9](OC)=[O:10])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([CH:13]2[CH2:15][CH2:14]2)[CH2:9][OH:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 59882236HCID 59882236, compound

Product 1

HCID 59882242HCID 59882242, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of methyl (2S)-(4-chlorophenyl)(cyclopropyl)ethanoate (7.72 g, 34.4 mmol) in methylene chloride (300 ml) at −78° C. under nitrogen is added diisobutyl aluminum hydride (86 ml of a 1.0 M solution in methylene chloride, 86.0 mmol). The reaction mixture is allowed to warm to room temperature and stirred for an additional hour. The reaction is quenched by the addition of saturated aqueous ammonium chloride and then filtered. The organic layer is separated, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel eluting with ether:hexane (15:85) to afford the title compound as a colorless liquid (5.45 g, 80%) which is characterized by 1HNMR, 13CNMR and mass spectral analyses.

Workup

  1. customThe reaction is quenched by the addition of saturated aqueous ammonium chloride
  2. filtrationfiltered
  3. customThe organic layer is separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is chromatographed on silica gel eluting with ether:hexane (15:85)

Sources & evidence

ORD record
ord-4970de166698450a9ad9986d29f4caa6
Source dataset
uspto-grants-2004_08
Patent number
US06770463B2

Reaction notes

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