Potassium Carbonate → tert-Butyl 4-[(3E)-2-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-4-(2-{[4-(trifluoromethoxy)-benzyl]oxy}phenyl)but-3-en-1-yl]benzoate

HRID 1920594Notes

Reaction equation

HRID 1920594 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20]([O:22][C:23](=[O:54])[CH2:24][C:25]1([CH2:28][CH2:29][CH:30](/[CH:45]=[CH:46]/[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[OH:53])[CH2:31][C:32]2[CH:44]=[CH:43][C:35]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[CH:34][CH:33]=2)[CH2:27][CH2:26]1)[CH3:21]>C(#N)C>[CH2:20]([O:22][C:23](=[O:54])[CH2:24][C:25]1([CH2:28][CH2:29][CH:30](/[CH:45]=[CH:46]/[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[O:53][CH2:8][C:7]2[CH:10]=[CH:11][C:4]([O:3][C:2]([F:13])([F:12])[F:1])=[CH:5][CH:6]=2)[CH2:31][C:32]2[CH:33]=[CH:34][C:35]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[CH:43][CH:44]=2)[CH2:26][CH2:27]1)[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzeneHCID 57965746tert-Butyl 4-[(3E)-2-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-4-(2-hydroxyphenyl)but-3-en-1-yl]benzoate

Product 1

HCID 57965772tert-Butyl 4-[(3E)-2-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-4-(2-{[4-(trifluoromethoxy)-benzyl]oxy}phenyl)but-3-en-1-yl]benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

118 mg (0.46 mmol) of 4-trifluoromethoxybenzyl bromide and 98 mg (0.71 mmol) of anhydrous potassium carbonate are added to a solution of 170 mg (0.36 mmol) of tert-butyl 4-[(3E)-2-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-4-(2-hydroxyphenyl)but-3-en-1-yl]benzoate in 3 ml of dry acetonitrile, and the mixture is heated under reflux for 12 hours. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. The organic phase is concentrated. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1). This gives 155 mg (67% of theory) of a colorless oil.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 12 hours
  3. concentrationThe mixture is then concentrated to dryness
  4. washwashed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationThe organic phase is concentrated

Sources & evidence

ORD record
ord-a4c7cf1e02fa4836abbfab62449e75ab
Source dataset
uspto-grants-2012_05
Patent number
US08168821B2

Reaction notes

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