Anisole → 1-Methoxy-4-(1-phenyl-cyclohexyl)-benzene

HRID 70733

반응식

HRID 70733 반응식
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]1([C:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCCCCCC.C(OCC)(=O)C>ClCCl.C(S([O-])(=O)=O)(F)(F)F.[Ag+]>[CH3:8][O:7][C:1]1[CH:6]=[CH:5][C:4]([C:15]2([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)=[CH:3][CH:2]=1

참가 물질

6

반응물 3

HCID 7519AnisoleHCID 130431-PhenylcyclohexeneHCID 21899848Ethylacetate heptane2회

생성물 1

HCID 116805591-Methoxy-4-(1-phenyl-cyclohexyl)-benzene

시약·촉매·용매 2

HCID 76223Silver(I) trifluoromethanesulfonate촉매HCID 6344Dichloromethane용매

실험 절차

A mixture of AuCl3 (7.6 mg, 0.025 mmol) and AgOTf (19.3 mg, 0.075 mmol) was stirred in dichloromethane (2 mL) for 30 min. Anisole (54 mg, 0.5 mmol) and 1-Phenyl-1-cyclohexene (158 mg, 1 mmol) were then added sequentially. The resulting mixture was stirred at room temperature overnight. Evaporation of the solvent under reduced pressure gave 130 mg of crude material. Flash chromatography (heptane:ethyl acetate 95:5) afforded 90 mg of a as a colorless oil. Rf=0.33 (heptane:ethyl acetate 95:5). 1H-NMR (400 MHz, CDCl3) δ 7.27-7.25 (m, 4H), 7.19 (d, 2H, J=8.8 Hz), 7.12 (m, 1H), 6.81 (d, 2H, J=8.8 Hz), 3.77 (s, 3H), 2.30-2.20 (m, 4H), 1.62-1.44 (m, 6H). 13C-NMR (100 MHz, CDCl3) δ 157.4, 149.2, 140.9, 128.4 (two carbons), 128.4 (two carbons), 127.3 (two carbons), 125.5, 113.8 (two carbons), 55.4, 45.9, 37.5 (two carbons), 26.7, 23.2 (two carbons).

후처리

  1. customEvaporation of the solvent under reduced pressure
  2. customgave 130 mg of crude material

출처 및 근거

ORD 기록
ord-73391136d8ff4870aa0d7c405de6649a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822548B2

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