5-(2,3-Difluorophenyl)nona-1,8-dien-5-ol → (Z)-1-(2,3-difluorophenyl)cyclohept-4-enol

HRID 1666116노트

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HRID 1666116 반응식
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([OH:18])([CH2:14][CH2:15][CH:16]=[CH2:17])[CH2:10][CH2:11]C=C>C(Cl)Cl.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([OH:18])[CH2:10][CH2:11][CH:17]=[CH:16][CH2:15][CH2:14]1

참가 물질

4

반응물 1

HCID 579114555-(2,3-Difluorophenyl)nona-1,8-dien-5-ol

생성물 1

HCID 57911478(Z)-1-(2,3-difluorophenyl)cyclohept-4-enol

시약·촉매·용매 2

HCID 178425456HCID 178425456, 화합물촉매HCID 6344Dichloromethane용매

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온도
45 °C

실험 절차

In a 500 mL round-bottomed flask (t=g) was added 5-(2,3-difluorophenyl)nona-1,8-dien-5-ol (1.15 g, 4.56 mmol) in CH2Cl2 (50 mL) to give a colorless solution. Grubbs II (0.193 g, 0.228 mmol) was added, and the mixture was heated at 45° C. for 19 hours. TLC showed clean conversion to a more polar spot. Combined material with 68908-184 and concentrated to dryness and the residue was subject to purification up to 50% Et2O/hexane. The major peak was pooled and concentrated to a colorless oil (0.761 g, 74.5%). 1H NMR showed the majority as the desired product (same as the later synthesized compound using Grubbs I catalyst) and a minor component with double-bond isomerized.

후처리

  1. customto give a colorless solution
  2. concentrationCombined material with 68908-184 and concentrated to dryness
  3. customthe residue was subject to purification up to 50% Et2O/hexane
  4. concentrationconcentrated to a colorless oil (0.761 g, 74.5%)

출처 및 근거

ORD 기록
ord-51483f9e3eb744f5a7d902df54568bbb
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044043B2

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