3-(4-t-Butyloxycarbonylphenyl)acrylic acid ethyl ester → Tert-butyl 4-(3-ethoxy-3-oxopropyl)benzoate

HRID 1252231Notes

Reaction equation

HRID 1252231 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:9][CH:8]=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:11][CH:12]=1)[CH3:2]

Participants

4

Reactant 1

HCID 537912813-(4-t-Butyloxycarbonylphenyl)acrylic acid ethyl ester

Product 1

HCID 9993703Tert-butyl 4-(3-ethoxy-3-oxopropyl)benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(4-t-butyloxycarbonylphenyl)acrylic acid ethyl ester (11.52 g) and 5% palladium-charcoal in ethanol (115 ml) was stirred under hydrogen atmosphere at room temperature. The catalyst was removed by filtration and washed with ethanol. The combined solution was evaporated to give 3-(4-tert-butyloxycarbonylphenyl)propionic acid ethyl ester.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with ethanol
  3. customThe combined solution was evaporated

Sources & evidence

ORD record
ord-f068d433740847b5ac8ad7a6e65cb2dc
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

Loading…