Methyl Acrylate → HCID 10340230, compound

HRID 322868Notes

Reaction equation

HRID 322868 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:16])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[C:30]([O:34][CH3:35])(=[O:33])[CH:31]=[CH2:32]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15](=[O:16])[CH:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:32][CH2:31][C:30]([O:34][CH3:35])=[O:33])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 10542398HCID 10542398, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10340230HCID 10340230, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of benzyl (3-benzyloxyphenyl) ketone (10 g) in tetrahydrofuran (100 mL) cooled at 0° C. is treated with potassium tert-butoxide (370 mg). After 40 minutes at 0° C., the mixture is treated with methyl acrylate (2.9 g) and stirring is continued at ambient temperature. The reaction is then concentrated under reduced pressure, partitioned between water and ethyl acetate and the organic layer is dried over magnesium sulphate. Concentration gives methyl (RS)-5-(3-benzyloxyphenyl)-5-oxo-4-phenylpentanoate (11.6 g), in the form of a colourless oil.

Workup

  1. customis continued at ambient temperature
  2. concentrationThe reaction is then concentrated under reduced pressure
  3. custompartitioned between water and ethyl acetate
  4. dry with materialthe organic layer is dried over magnesium sulphate
  5. concentrationConcentration

Sources & evidence

ORD record
ord-3b58c3da74dd4c698dd25e9e2ff26c80
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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