1,3-Butadienyl acetate → 4-((1E,3E)-4-Methoxycarbonyl-buta-1,3-dienyl) 3-methyl-benzoic acid tert-butyl ester

HRID 220825Notes

Reaction equation

[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10](Br)=[C:9]([CH3:14])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C(O[CH:20]=[CH:21][CH:22]=C)(=O)C.[C:24]([O-:27])(=[O:26])[CH3:25].[Na+].[CH3:29]C(N(C)C)=O>C1C=CC([P]([Pd]([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)=CC=1>[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10](/[CH:20]=[CH:21]/[CH:22]=[CH:25]/[C:24]([O:27][CH3:29])=[O:26])=[C:9]([CH3:14])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 140 °C

Procedure

Tetrakis(triphenylphosphine)palladium (0) (852 mg, 0.7 mol) was added to a stirred solution of 4-bromo-3-methyl-benzoic acid tert-butyl ester from Example E31.1 (1.86 g, 6.8 mmol), 1-acetoxy-1,3-butadiene (7.5 ml, 64.5 mmol) and sodium acetate (5.69 g, 69.4 mmol) in DMA (75 ml). The mixture was heated at 140° C. for 3 h, filtered through Celite® filter agent and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 20% EtOAc:80% pet. ether) to yield the title compound (1.54 g, 74%).

Workup

filtrationfiltered through Celite®
filtrationfilter agent
concentrationthe filtrate was concentrated in vacuo
customThe residue was purified by flash chromatography on silica gel (eluant; 20% EtOAc:80% pet. ether)

Sources & evidence

ORD record: ord-29b891823bc34f16953784aaf07c24b2
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202858B2

Reaction notes

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