Triethylamine → tert-butyl 4-[2-[(E)-(4-tert-butylphenyl)methylideneamino]oxyethoxy]-2-[4-(trifluoromethyl)benzoyl]oxybenzoate

HRID 29650

反応式

HRID 29650 の反応式
[C:1]([O:5][C:6](=[O:30])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][O:16][N:17]=[CH:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=2)=[CH:9][C:8]=1[OH:29])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[F:38][C:39]([F:50])([F:49])[C:40]1[CH:48]=[CH:47][C:43]([C:44](Cl)=[O:45])=[CH:42][CH:41]=1>C(Cl)Cl.[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:30])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][O:16]/[N:17]=[CH:18]/[C:19]2[CH:20]=[CH:21][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:23][CH:24]=2)=[CH:9][C:8]=1[O:29][C:44](=[O:45])[C:43]1[CH:47]=[CH:48][C:40]([C:39]([F:38])([F:49])[F:50])=[CH:41][CH:42]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 865973854-[2-(4-Tert-butyl-benzylideneaminooxy)-ethoxy]-2-hydroxy-benzoic acid tert-butyl ester

生成物 1

HCID 87734367tert-butyl 4-[2-[(E)-(4-tert-butylphenyl)methylideneamino]oxyethoxy]-2-[4-(trifluoromethyl)benzoyl]oxybenzoate収率 96.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution of 4-[2-(4-tert-butyl-benzylideneaminooxy)-ethoxy]-2-hydroxy-benzoic acid tert-butyl ester (0.298 g, 0.72 mmol) in methylene chloride (10 mL) was added triethylamine (0.200 mL, 1.43 mmol) and 4-trifluoromethyl benzoyl chloride (0.200 mL, 1.42 mmol). The reaction was stirred at room temperature overnight, poured into brine and the aqueous layer extracted with ethyl acetate. The combined organics dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (8/92) to afford 4-{2-[({(E)-[4-(tert-butyl)phenyl]methylidene}amino)oxy]ethoxy}-2-{[4-(trifluoromethyl)benzoyl]oxy}benzoic acid tert-butyl ester (0.405 g, 96%) as a colorless oil. 1H NMR (300 MHz, CDCl3); δ 8.33 (d, 2H), 8.12 (s, 1H), 7.97 (d, 1H), 7.78 (d, 2H), 7.52 (d, 2H), 7.38 (d, 2H), 6.92 (dd, 1H), 6.76 (d, 1H), 4.50 (t, 2H), 4.33 (t, 2H), 1.40 (s, 9H), 1.30 (s, 9H).

後処理

  1. extractionthe aqueous layer extracted with ethyl acetate
  2. dry with materialThe combined organics dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-d8ffc7ad244542f48f2c35b36b2adef0
出典データセット
uspto-grants-2008_09
特許番号
US07420083B2

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