Triethylamine → Ethyl 3-[3-(4-methoxybenzoyl)phenyl]prop-2-enoate

HRID 1285011Notes

Reaction equation

HRID 1285011 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:6].[C:18]([O:22][CH2:23][CH3:24])(=[O:21])[CH:19]=[CH2:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]([C:4]2[CH:3]=[C:2]([CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:19][C:18]([O:22][CH2:23][CH3:24])=[O:21])=[O:6])=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 11776TriphenylphosphineHCID 2757031(3-bromophenyl)(4-methoxyphenyl)methanone

Product 1

HCID 53737127Ethyl 3-[3-(4-methoxybenzoyl)phenyl]prop-2-enoate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-bromo-4'-methoxybenzophenone (Allen, Schumann, Day and Van Campen, J. Amer. Chem. Soc., 1958, 80, 591) (14.6 g), ethyl acrylate (25.3 g), palladium (II) acetate (100 mg), triphenylphosphine (225 mg) and triethylamine (2.65 g) in acetonitrile (20 mL) was heated in a stainless steel autoclave under a nitrogen atmosphere at 155° for 5 hours. After cooling, water was added and the precipitated solid was recrystallized from methanol to yielded ethyl 3-(4-methoxy benzoyl)cinnamate, m.p. 71°-71.5° (5.6 g).

Workup

  1. temperatureAfter cooling
  2. customthe precipitated solid was recrystallized from methanol

Sources & evidence

ORD record
ord-2c420beabda142f79f652803004e53aa
Source dataset
uspto-grants-1986_01
Patent number
US04564685

Reaction notes

Loading…