Hydrochloric Acid → 1-(2,4-Dimethyl-5-oxazolyl)-1-(3-furyl)-2,2,2-trifluoroethanol

HRID 2830

Reaction equation

HRID 2830 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:19]1[CH:23]=[CH:22][C:21]([C:24]([C:26]2[O:30][C:29]([CH3:31])=[N:28][C:27]=2[CH3:32])=[O:25])=[CH:20]1.[F:33][C:34]([Si](C)(C)C)([F:36])[F:35].Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:31][C:29]1[O:30][C:26]([C:24]([C:21]2[CH:22]=[CH:23][O:19][CH:20]=2)([OH:25])[C:34]([F:36])([F:35])[F:33])=[C:27]([CH3:32])[N:28]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 537121082,4-Dimethyl-5-oxazolyl 3-furyl ketone

Product 1

HCID 189363371-(2,4-Dimethyl-5-oxazolyl)-1-(3-furyl)-2,2,2-trifluoroethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (250 mg) was added to a stirred solution of 2,4-dimethyl-5-oxazolyl 3-furyl ketone (1.7 g) and (trifluoromethyl) trimethylsilane (1.9 g) in dry tetrahydrofuran (30 ml) at -10° C. The mixture was allowed to warm to room temperature. After 45 minutes 6M hydrochloric acid (30 ml) was added. After 1 hour the mixture was basified by the addition of saturated aqueous sodium hydrogen carbonate and then extracted with dichloromethane. The material thus obtained was purified by flash chromatography and recrystallisation from diethyl ether.

Workup

  1. extractionextracted with dichloromethane
  2. customThe material thus obtained
  3. customwas purified by flash chromatography and recrystallisation from diethyl ether

Sources & evidence

ORD record
ord-9e8f852e5b4a473880332d65fd05ff5a
Source dataset
uspto-grants-1998_03
Patent number
US05731335

Linked notes

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