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

HRID 1268451

반응식

HRID 1268451 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][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:4]=2[CH:3]=1.[CH:21]([C:23]1[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=1)=[CH2:22].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][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4]2[C:3](/[CH:22]=[CH:21]/[C:23]3[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=3)=[CH:2][CH:11]=[CH:10][C:9]1=2

참가 물질

6

반응물 3

HCID 80271Tri-o-tolylphosphineHCID 10866858Ethyl 4-vinylbenzoateHCID 158960184,4-Dimethyl-7-bromo-1-phenylthio-3,4-dihydronaphthalene

생성물 1

HCID 19695074Ethyl (E)-4-[2-(5,6-dihydro-5,5-dimethyl-8-(phenylthio)naphthalenyl)ethenyl]benzoate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8471Triethylamine용매

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온도
90 °C

실험 절차

To a degassed solution of 0.35 g (1.0 mmol) of 2-bromo-5,6 -dihydro-5,5-dimethyl-8-(phenylthio)-naphthalene (Compound A35) and 0.34 g (1.9 mmol) of ethyl 4-vinylbenzoate in 4.0 mL of triethylamine, was added 0.066 g (0.2 mmol) of tri-o-tolylphosphine and then 0.025 g (0.1 mmol) of palladium(II) acetate. The reaction was heated at 90° C. for 2.25 h. The reaction was concentrated in vacua. The residue was purified by flash chromatography (silica, 5% ethyl acetate in hexane), followed by recrystallization using EtOH to afford the title compound as white crystals.

후처리

  1. concentrationThe reaction was concentrated in vacua
  2. customThe residue was purified by flash chromatography (silica, 5% ethyl acetate in hexane)
  3. customfollowed by recrystallization

출처 및 근거

ORD 기록
ord-823399b56a85447a867c10230d5890db
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06555690B2

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