Tetrahydrofuran → HCID 67073912, compound

HRID 2103427Notes

Reaction equation

HRID 2103427 reaction equation
C[C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[S:5]C=1CO.[H-].[Na+].[CH3:21][O:22][C:23](=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[C:26](CBr)[CH:25]=1.[CH2:33]1[CH2:37][O:36][CH2:35][CH2:34]1>CCOCC>[CH3:21][O:22][C:23](=[O:32])[C:24]1[CH:25]=[CH:26][C:27]([CH:35]([C:34]2[S:5][CH:4]([C:9]3[CH:10]=[CH:11][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:13][CH:14]=3)[N:3]([CH3:2])[CH:33]=2)[O:36][CH3:37])=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 517981Methyl 3-(bromomethyl)benzoateHCID 2783005(4-Methyl-2-(4-(trifluoromethyl)phenyl)-1,3-thiazol-5-yl)methanol

Product 1

HCID 67073912HCID 67073912, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Cool (0° C.) a solution of 2-([4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl)-methanol (450 mg, 1.64 mmol) in THF and add NaH (70 mg, 50% dispersion in mineral oil, 1.75 mmol). Stir the resulting mixture for 5 min. Remove the cold bath and continue stirring for 1 hr. To this mixture add 3-(bromomethyl)-benzoic acid methyl ester (450 mg, 1.95 mmol). Stir the resulting mixture for 3 hr then quench the reaction with sat. NH4Cl solution. Dilute the mixture with ether, wash with brine, dry over MgSO4 and concentrate under vacuum. Purify the residue by flash chromatography (eluting with 30% ethyl acetate in heptane) to give the title compound (181 mg) as an oil.

Workup

  1. customRemove the cold bath
  2. stirringcontinue stirring for 1 hr
  3. stirringStir the resulting mixture for 3 hr
  4. customthen quench
  5. customthe reaction with sat. NH4Cl solution
  6. washwash with brine
  7. dry with materialdry over MgSO4
  8. concentrationconcentrate under vacuum
  9. customPurify the residue
  10. washby flash chromatography (eluting with 30% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-40c7578a7de5464aa5ab60ad3a986264
Source dataset
uspto-grants-2009_08
Patent number
US07576109B2

Reaction notes

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