Triethylamine → 3-[4-(5-tert-Butyl-2-methyl-phenylethynyl)-phenyl]-acrylic acid ethyl ester

HRID 1869952Notes

Reaction equation

HRID 1869952 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([C:12]#[CH:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:14]([O:16][C:17](=[O:27])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][C:23](I)=[CH:22][CH:21]=1)[CH3:15].C(N(CC)CC)C.C(OCC)(=O)C>CCCCCC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:14]([O:16][C:17](=[O:27])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][C:23]([C:13]#[C:12][C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=[CH:9][C:8]=2[CH3:11])=[CH:22][CH:21]=1)[CH3:15]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 211071904-tert-Butyl-2-ethynyl-1-methyl-benzene2×HCID 541932622-Propenoic acid, 3-(4-iodophenyl)-, ethyl ester

Product 1

HCID 690739133-[4-(5-tert-Butyl-2-methyl-phenylethynyl)-phenyl]-acrylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8058HexaneSolvent

Procedure

Following General Procedure B and using 4-tert-butyl-2-ethynyl-1-methyl-benzene (Intermediate 110, 0.08 g, 0.47 mmol), ethyl-4-iodocinnamate (0.12 g, 0.4 mmol), triethyl amine (8 mL), copper(I)iodide (0.019 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.07 g, 0.1 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 2-4% ethyl acetate in hexane as the eluent, the title compound was obtained (0.09 g, 55%).

Sources & evidence

ORD record
ord-32840fa616a74044acbee87d63cf779c
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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