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

HRID 1170555ノート

反応式

HRID 1170555 の反応式
[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

参加物

6

反応物 3

HCID 7519AnisoleHCID 130431-PhenylcyclohexeneHCID 21899848Ethylacetate heptane2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 76223Silver(I) trifluoromethanesulfonate触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-2427b312744e453c81da4d12f8664385
出典データセット
uspto-grants-2010_11
特許番号
US07825265B2

反応ノート

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