Hydrochloric Acid → HCID 67547192, compound

HRID 2356725Notes

Reaction equation

HRID 2356725 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[N:9][C:8]=2[C:19](OC)=[O:20])=[CH:4][CH:3]=1.[BH4-].[Li+].O.Cl>O1CCCC1>[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[N:9][C:8]=2[CH2:19][OH:20])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4148881Lithium borohydrideHCID 67546985HCID 67546985, compound

Product 1

HCID 67547192HCID 67547192, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(5-chlorothiophen-2-yl)-2-(4-fluorophenyl)-4-methoxycarbonyloxazole (1.8 g) and lithium borohydride (580 mg) in tetrahydrofuran (40 ml) was stirred at room temperature for one hour, and then, refluxed for 1.5 hours. After cooling, water and 10% hydrochloric acid were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The resulting residue was triturated with diethyl ether-ethyl acetate to obtain 5-(5-chlorothiophen-2-yl)-2-(4-fluoro-phenyl)-4-hydroxymethyloxazole (1.48 g) as colorless powder.

Workup

  1. temperaturerefluxed for 1.5 hours
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe resulting residue was triturated with diethyl ether-ethyl acetate

Sources & evidence

ORD record
ord-14b02251e4bb486eb5bd5fb3433e9c6f
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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