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 1913787Notes

Reaction equation

HRID 1913787 reaction equation
[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]

Participants

5

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9f768cd3b26b4f9db3c97936a01706a0
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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