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

HRID 965490

반응식

HRID 965490 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

반응 조건

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 vacuo. 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 vacuo
  2. customThe residue was purified by flash chromatography (silica, 5% ethyl acetate in hexane)
  3. customfollowed by recrystallization

출처 및 근거

ORD 기록
ord-b8ee9d94292e43ad9d037d4aaa1e830e
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05773594

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