Ethanol → (E)-3-Cyclopentyl-2-(4-methylsulfanyl-phenyl)-acrylic acid ethyl ester

HRID 2103606Notes

Reaction equation

HRID 2103606 reaction equation
[CH2:1]([O:3][C:4](=[O:13])/[C:5](/Br)=[CH:6]/[CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[CH3:2].[CH3:14][S:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:13])/[C:5](/[C:19]1[CH:20]=[CH:21][C:16]([S:15][CH3:14])=[CH:17][CH:18]=1)=[CH:6]/[CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27339594-(Methylthio)phenylboronic acidHCID 86605124(Z)-2-bromo-3-cyclopentyl-acrylic acid ethyl ester

Product 1

HCID 67084466(E)-3-Cyclopentyl-2-(4-methylsulfanyl-phenyl)-acrylic acid ethyl esterYield 85.6%

Reagents, catalysts & solvents 2

HCID 178420553HCID 178420553, compoundCatalystHCID 1140TolueneSolvent

Procedure

Following the method of example 54c, reaction of (Z)-2-bromo-3-cyclopentyl-acrylic acid ethyl ester (56.8 g, 229 mmol) with 4-(methylthio)benzene boronic acid (46.3 g, 276 mmol) and tetrakis(triphenylphosphino)palladium(0) (10.4 g, 3 mol %) in a mixture of toluene (1600 ml), ethanol (421 ml) and 2 M aqueous sodium carbonate solution (420 ml) affords the title compound as an oil (56.9 g). MS (m/e): 291.2 (M+H).

Sources & evidence

ORD record
ord-4a9414ef3126464ca37721e63a51bc71
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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