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

HRID 220825
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HRID 220825 반응식
[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]
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6

반응물 4

HCID 151951,3-Butadienyl acetateHCID 31374DimethylacetamideHCID 517045Sodium AcetateHCID 11845988Tert-butyl 4-bromo-3-methylbenzoate

생성물 1

HCID 866266384-((1E,3E)-4-Methoxycarbonyl-buta-1,3-dienyl) 3-methyl-benzoic acid tert-butyl ester수율 74%

시약·촉매·용매 1

HCID 178418397
HCID 178418397, 화합물
촉매

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온도
140 °C

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-29b891823bc34f16953784aaf07c24b2
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08202858B2

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