Sodium hydride → HCID 59556324, compound

HRID 1172690Notes

Reaction equation

HRID 1172690 reaction equation
C(OP([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[C:12]([F:18])[CH:11]=1)(=O)OCC)C.[H-].[Na+].[CH3:21][C:22]1[N:23]=[C:24]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)[S:25][C:26]=1[C:27](=O)[CH2:28][CH2:29][CH2:30][CH3:31]>O1CCCC1>[F:18][C:12]1[CH:11]=[C:10](/[CH:9]=[C:27](/[C:26]2[S:25][C:24]([C:33]3[CH:34]=[CH:35][C:36]([C:39]([F:41])([F:42])[F:40])=[CH:37][CH:38]=3)=[N:23][C:22]=2[CH3:21])\[CH2:28][CH2:29][CH2:30][CH3:31])[CH:15]=[CH:14][C:13]=1[C:16]#[N:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 59556333HCID 59556333, compoundHCID 59556379HCID 59556379, compound

Product 1

HCID 59556324HCID 59556324, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.0 g (4-Cyano-3-fluoro-benzyl)-phosphonic acid diethyl ester was dissolved in 50 ml tetrahydrofuran and cooled in an ice bath. At 0° C. 103 mg sodium hydride were added and the mixture stirred for fifteen minutes. Then 1.2 g 1-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-pentan-1-one, dissolved in 20 ml tetrahydrofuran, were added dropwise. The cooling bath was removed and the reaction mixture stirred at room temperature for two hours. Then 1.0 g (4-Cyano-3-fluoro-benzyl)-phosphonic acid diethyl ester and 103 mg sodium hydride were added and the reaction mixture stirred for an additional hour. Then 20 ml water were added and the mixture extracted five times with portions of 25 ml ethyl acetate. The combined organic layers were dried over MgSO4, then the solvent was removed in vacuo to obtain 1.6 g 2-Fluoro-4-{(E)-2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-hex-1-enyl}-benzonitrile as a yellow oil.

Workup

  1. temperaturecooled in an ice bath
  2. customAt 0° C
  3. additionwere added dropwise
  4. customThe cooling bath was removed
  5. stirringthe reaction mixture stirred at room temperature for two hours
  6. additionThen 1.0 g (4-Cyano-3-fluoro-benzyl)-phosphonic acid diethyl ester and 103 mg sodium hydride were added
  7. stirringthe reaction mixture stirred for an additional hour
  8. additionThen 20 ml water were added
  9. extractionthe mixture extracted five times with portions of 25 ml ethyl acetate
  10. dry with materialThe combined organic layers were dried over MgSO4
  11. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ce3a0121db464210b1dc22a934052995
Source dataset
uspto-grants-2010_11
Patent number
US07834030B2

Reaction notes

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