Potassium Carbonate → Methyl 4-[(4E)-3-(4-cyanobenzyl)-5-(2-{4-[4-(trifluoromethyl)phenoxy]butoxy}phenyl)pent-4-en-1-yl]benzoate

HRID 1913798Notes

Reaction equation

HRID 1913798 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1/[CH:13]=[CH:14]/[CH:15]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][CH:30]=1)[CH2:16][CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1.[F:37][C:38]([F:47])([F:46])[C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:35]([C:32]1[CH:33]=[CH:34][C:29]([CH2:28][CH:15](/[CH:14]=[CH:13]/[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH2:4][CH2:3][CH2:2][O:45][C:42]2[CH:43]=[CH:44][C:39]([C:38]([F:37])([F:46])[F:47])=[CH:40][CH:41]=2)[CH2:16][CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=2)=[CH:30][CH:31]=1)#[N:36]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 678744-(Trifluoromethyl)phenolHCID 59180489Methyl 4-[(4E)-5-[2-(4-bromobutoxy)phenyl]-3-(4-cyanobenzyl)pent-4-en-1-yl]benzoate

Product 1

HCID 59180514Methyl 4-[(4E)-3-(4-cyanobenzyl)-5-(2-{4-[4-(trifluoromethyl)phenoxy]butoxy}phenyl)pent-4-en-1-yl]benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 392 mg (0.72 mmol) of methyl 4-[(4E)-5-[2-(4-bromobutoxy)phenyl]-3-(4-cyanobenzyl)pent-4-en-1-yl]benzoate in 10 ml of dry acetonitrile is mixed with 174 mg (1.08 mmol) of 4-trifluoromethylphenol and 148 mg (1.08 mmol) of anhydrous potassium carbonate and then heated under reflux for 12 h. The mixture is subsequently filtered, and the filtrate is evaporated to dryness. 450 mg (0.61 mmol, purity 86%, 86% of theory) of a yellowish oil are isolated.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12 h
  3. filtrationThe mixture is subsequently filtered
  4. customthe filtrate is evaporated to dryness
  5. custom450 mg (0.61 mmol, purity 86%, 86% of theory) of a yellowish oil are isolated

Sources & evidence

ORD record
ord-39e634b483954c368ab3f07f2db6cc7e
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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