1-Chloro-4-(4-methoxy-benzyloxymethyl)-2-trifluoromethyl-benzene → 1-Cyclohexyl-4-(4-methoxy-benzyloxymethyl)-2-trifluoromethyl-benzene

HRID 2100659

反応式

HRID 2100659 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].[Br-].[CH:24]1([Zn+])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C1COCC1>CN1CCCC1=O.CC(P(C(C)(C)C)C(C)(C)C)(C)C.CC(P(C(C)(C)C)C(C)(C)C)(C)C.[Pd]>[CH:24]1([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:4][C:3]=2[C:19]([F:22])([F:21])[F:20])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

参加物

5

反応物 2

HCID 220577531-Chloro-4-(4-methoxy-benzyloxymethyl)-2-trifluoromethyl-benzeneHCID 178420634HCID 178420634、化合物

生成物 1

HCID 220577361-Cyclohexyl-4-(4-methoxy-benzyloxymethyl)-2-trifluoromethyl-benzene

試薬・触媒・溶媒 2

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)触媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
105 °C

実験手順

1-Chloro-4-(4-methoxy-benzyloxymethyl)-2-trifluoromethyl-benzene (2 g, 6.51 mmol), Pd(t-Bu3P)2 (66.54 mg, 0.13 mmol) and cyclohexylzinc bromide/THF solution (0.5 M, 40 mL, 19.5 mmol) are mixed in 1-methyl-2-pyrrolidinone (NMP) (40 mL). The mixture is purged with N2 (g) and then heated at 105° C. for 16 hours. The reaction mixture is poured into saturated aqueous NH4Cl (250 mL) and extracted with EtOAc. The combined extracts are washed with brine and dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (8:1 hexanes/EtOAc) to give 1-Cyclohexyl-4-(4-methoxy-benzyloxymethyl)-2-trifluoromethyl-benzene. To a solution of this material in DCM (8 mL) is added TFA (8 mL). The reaction mixture is stirred at room temperature for 16 hours. After concentration, the residue is partitioned between saturated aqueous NH4Cl and EtOAc. The aqueous phase is extracted with EtOAc. The combined organic extracts are washed with brine and dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (4:1 hexanes/EtOAc) to give (4-Cyclohexyl-3-trifluoromethyl-phenyl)-methanol.

後処理

  1. customThe mixture is purged with N2 (g)
  2. additionThe reaction mixture is poured into saturated aqueous NH4Cl (250 mL)
  3. extractionextracted with EtOAc
  4. washThe combined extracts are washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentration
  7. customthe residue is purified by silica gel chromatography (8:1 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-6b48956177ce4795a4f1736d1c999e7c
出典データセット
uspto-grants-2009_08
特許番号
US07572811B2

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