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 1913787ノート

反応式

HRID 1913787 の反応式
[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]

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9f768cd3b26b4f9db3c97936a01706a0
出典データセット
uspto-grants-2013_12
特許番号
US08609727B2

反応ノート

読み込み中…