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Tri-o-tolylphosphine → Ethyl (E)-4-[-2-(5,6-dihydro-5,5-dimethyl-8-(ethylthio)-naphthalen-2-yl)ethenyl]benzoate

HRID 1371
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인쇄 미리보기

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HRID 1371 반응식
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:8]([CH3:13])([CH3:12])[CH2:7][CH:6]=[C:5]([S:14][CH2:15][CH3:16])[C:4]=2[CH:3]=1.[CH:17]([C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1)=[CH2:18].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:12][C:8]1([CH3:13])[CH2:7][CH:6]=[C:5]([S:14][CH2:15][CH3:16])[C:4]2[CH:3]=[C:2](/[CH:18]=[CH:17]/[C:19]3[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=3)[CH:11]=[CH:10][C:9]1=2
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참가 물질

6

반응물 3

HCID 80271Tri-o-tolylphosphineHCID 10866858Ethyl 4-vinylbenzoateHCID 225715212-Bromo-5,6-dihydro-5,5-dimethyl8-(ethylthio)-naphthalene

생성물 1

HCID 86586452Ethyl (E)-4-[-2-(5,6-dihydro-5,5-dimethyl-8-(ethylthio)-naphthalen-2-yl)ethenyl]benzoate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매
HCID 8471
Triethylamine
용매

반응 조건

온도
90 °C

실험 절차

To a degassed solution of 0.50 g (1.7 mmol) of 2-bromo-5,6-dihydro-5,5-dimethyl-8-(ethylthio)-naphthalene (Compound A36) and 0.45 g (2.5 mmol) of ethyl 4-vinylbenzoate in 4.0 mL of triethylamine, was added 109 mg (0.36 mmol) of tri-o-tolylphosphine and then 35 mg (0.16 mmol) of palladium(II) acetate. The reaction was heated at 90° C. for 2.25 h. The reaction was concentrated in vacuo and purified by flash chromatography (silica, 2% ethyl acetate in hexane) to afford the title compound as a colorless oil.

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by flash chromatography (silica, 2% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-b1bd58830652436484aeb0d21b29efe6
출처 데이터셋
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05723666

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