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

HRID 29650

Reaction equation

HRID 29650 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d8ffc7ad244542f48f2c35b36b2adef0
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Linked notes

Loading…