Acetic Acid → Ethyl 2-chloro-3-hydroxy-3-phenylpropionate

HRID 567419Notes

Reaction equation

HRID 567419 reaction equation
[Cl:1][CH:2]([C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(O)(=O)C>ClCCl.CCOCC.O.[BH4-].[Zn+2].[BH4-]>[Cl:1][CH:2]([CH:8]([OH:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

7

Reactant 2

HCID 176Acetic AcidHCID 9855991Ethyl 2-chloro-3-oxo-3-phenylpropanoate

Product 1

HCID 12714561Ethyl 2-chloro-3-hydroxy-3-phenylpropionate

Reagents, catalysts & solvents 4

HCID 12838295ZINC;boranuideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 2-chloro-3-oxo-3-phenylpropionate (CI, EXAMPLE 1, 6.8 g, 30 mmol) in dichloromethane (68 ml) is cooled to −5° and a solution of zinc borohydride (0.4 M, 38 ml, 15 mmol) in ether is added dropwise over 30 mins. After the addition, the reaction mixture is stirred at 0° for 30 mins and then poured into a cold solution (0°) of acetic acid (5 ml) in water (15 ml). The resulting mixture is extracted with dichloromethane (30 ml×2). The combined organic extracts are washed with water (30 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue is chromatographed (silica gel; ethyl acetate/hexane, (5/95 to 25/75) to give the title compound which is a 1:9 mixture of anti and syn isomers as determined by NMR.

Workup

  1. temperatureis cooled to −5°
  2. additionAfter the addition
  3. extractionThe resulting mixture is extracted with dichloromethane (30 ml×2)
  4. washThe combined organic extracts are washed with water (30 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is chromatographed (silica gel

Sources & evidence

ORD record
ord-8bb608cecb0d43cb879c07233b557537
Source dataset
uspto-grants-2001_01
Patent number
US06177573B1

Reaction notes

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