Pyridine → methyl 2(S)-phenoxycarbonyloxy-3-phenylpropionate

HRID 259833Notes

Reaction equation

HRID 259833 reaction equation
[OH:1][C@@H:2]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].N1C=CC=CC=1.[C:20](Cl)(=[O:28])[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl>[O:21]([C:20]([O:1][C@@H:2]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4])=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 5289077(S)-methyl 2-hydroxy-3-phenylpropanoate

Product 1

HCID 22861691methyl 2(S)-phenoxycarbonyloxy-3-phenylpropionateYield 114.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To methyl 2(S)-hydroxy-3-phenylpropionate (5.0 g) and pyridine (8.78 g) in methylene chloride (50 ml) was dropwise added phenyl chlorocarbonate (4.78 g) under cooling at 0°-10° C. over 30 minutes. After the dropwise addition, the mixture was stirred at said temperature for 60 minutes, washed with 10% hydrochloric acid and water, dried over magnesium sulfate, and concentrated to dryness under reduced pressure. As a result, 9.51 g of methyl 2(S)-phenoxycarbonyloxy-3-phenylpropionate was obtained as a pale yellow, oily substance.

Workup

  1. temperatureunder cooling at 0°-10° C. over 30 minutes
  2. additionAfter the dropwise addition
  3. customfor 60 minutes
  4. washwashed with 10% hydrochloric acid and water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-739296bb22a647bb985b777b9dfefdab
Source dataset
uspto-grants-1996_06
Patent number
US05523410

Reaction notes

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