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

HRID 2100659

반응식

HRID 2100659 반응식
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

참가 물질

5

반응물 2

HCID 220577531-Chloro-4-(4-methoxy-benzyloxymethyl)-2-trifluoromethyl-benzeneHCID 178420634HCID 178420634, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)촉매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
105 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6b48956177ce4795a4f1736d1c999e7c
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572811B2

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