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

HRID 2177054Notes

Reaction equation

HRID 2177054 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-18b261bf7098406dbbbdbe3759d04c1a
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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