Hydrochloric Acid → {4-Methyl-2-[3-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methanol

HRID 1257375Notes

Reaction equation

HRID 1257375 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[S:5][C:6]=1[C:7](OCC)=[O:8].[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].Cl>C(O)C.O1CCCC1>[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=2)[S:5][C:6]=1[CH2:7][OH:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2774390ethyl 4-methyl-2-[3-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylateHCID 4311764Sodium borohydrideHCID 5284359Calcium Chloride

Product 1

HCID 22647518{4-Methyl-2-[3-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methanolYield 50%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Under a nitrogen atmosphere at 0° C., to a mixed solution of the compound (380 mg, 1.2 mmol) obtained in Example 70a in ethanol/tetrahydrofuran (v/v=1/1, 6 mL) were added calcium chloride (500 mg, 4.5 mmol) and sodium tetrahydroborate (170 mg, 4.5 mmol), and the mixture was stirred at room temperature overnight. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=65/35) to give the title compound (160 mg, 50%) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=65/35)

Sources & evidence

ORD record
ord-1b38e857379d46ebbc263b32a70237a2
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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