Potassium Carbonate → Methyl 4-{(4E)-3-(4-cyanobenzyl)-5-[2-({4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]benzyl}-oxy)phenyl]pent-4-en-1-yl}benzoate

HRID 1913787노트

반응식

HRID 1913787 반응식
[C:1]([C:3]1[CH:31]=[CH:30][C:6]([CH2:7][CH:8](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[OH:29])[CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)#[N:2].Cl[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]([F:49])([C:45]([F:48])([F:47])[F:46])[C:41]([F:44])([F:43])[F:42])=[CH:36][CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH2:33][C:34]2[CH:35]=[CH:36][C:37]([C:40]([F:49])([C:41]([F:42])([F:43])[F:44])[C:45]([F:47])([F:48])[F:46])=[CH:38][CH:39]=2)[CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:30][CH:31]=1)#[N:2]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 205387711-Chloromethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-benzeneHCID 57831354methyl E-4-[3-(4-cyanobenzyl)-5-(2-hydroxyphenyl)pent-4-enyl]benzoate

생성물 1

HCID 59180492Methyl 4-{(4E)-3-(4-cyanobenzyl)-5-[2-({4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]benzyl}-oxy)phenyl]pent-4-en-1-yl}benzoate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 150 mg (0.365 mmol) of methyl E-4-[3-(4-cyanobenzyl)-5-(2-hydroxyphenyl)pent-4-enyl]benzoate (enantiomer 1, Example 51A) in 3 ml of dry acetonitrile is mixed with 139 mg (0.47 mmol) of 1-(chloromethyl)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]benzene [prepared as described in EP 0 009 787-A2] and 100 mg (0.73 mmol) of anhydrous potassium carbonate and then heated under reflux for 12 h. The mixture is then filtered and the filtrate is evaporated to dryness. The residue is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1). 210 mg (0.31 mmol, 86% of theory) of an oil are isolated.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 12 h
  3. filtrationThe mixture is then filtered
  4. customthe filtrate is evaporated to dryness
  5. customThe residue is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1)
  6. custom210 mg (0.31 mmol, 86% of theory) of an oil are isolated

출처 및 근거

ORD 기록
ord-9f768cd3b26b4f9db3c97936a01706a0
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609727B2

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