1-(3-Chlorophenyl)ethanone → (1S)-1-(3-CHLOROPHENYL)ETHANOL

HRID 1364476Notes

Reaction equation

HRID 1364476 reaction equation
B.O1CCCC1.[CH3:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=1)=[O:9]>C1(C)C=CC=CC=1.O1CCCC1>[Cl:16][C:12]1[CH:11]=[C:10]([C@@H:8]([OH:9])[CH3:7])[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 149331-(3-Chlorophenyl)ethanoneHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 6950741(1S)-1-(3-CHLOROPHENYL)ETHANOLYield 102.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of borane-tetrahydrofuran (77.6 mL, 77.62 mmol, Aldrich, 1 M solution in THF) and (R)-MeCBS (12.9 mL, 12.9 mmol, Aldrich, 1M solution in toluene) was added a solution of 3-chloroacetophenone (20.0 g, 129.37 mmol) in anhydrous tetrahydrofuran slowly over 30 min at room temperature. After complete addition, the reaction mixture was stirred for 10 min, quenched with 2N hydrochloric acid over 30 min. The reaction mixture was extracted with ether, dried, filtered and concentrated to afford 20.8 g of (S)-1-(3-chlorophenyl)ethanol as a viscous liquid.

Workup

  1. additionAfter complete addition
  2. customquenched with 2N hydrochloric acid over 30 min
  3. extractionThe reaction mixture was extracted with ether
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7948dfcde4a94d6bb0d9cbab90600c6d
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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