Lithium borohydride → (5-Benzyl-2-(2,5-difluorophenyl)oxazol-4-yl)methanol

HRID 404847Notes

Reaction equation

HRID 404847 reaction equation
[CH2:1]([C:8]1[O:12][C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[N:10][C:9]=1[C:21](OCC)=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[BH4-]>C1COCC1>[CH2:1]([C:8]1[O:12][C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[N:10][C:9]=1[CH2:21][OH:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 67450146Ethyl 5-benzyl-2-(2,5-difluorophenyl)oxazole-4-carboxylate

Product 1

HCID 67451532(5-Benzyl-2-(2,5-difluorophenyl)oxazol-4-yl)methanolYield 88.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-benzyl-2-(2,5-difluorophenyl)oxazole-4-carboxylate (590 mg, 1.72 mmol) in THF (8.6 mL) was slowly added LiBH4 (56.2 mg, 2.58 mmol) at room temperature. The reaction mixture was stirred for overnight. After quenched with water, the reaction mixture was extracted with EtOAc. The organic layers was washed with saturated NaHCO3 solution and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by automatic column chromatography (0 to 100% EtOAc in Hexanes) to yield (5-benzyl-2-(2,5-difluorophenyl)oxazol-4-yl)methanol (460 mg, 88%) as a white solid. LC/MS (uplc): MH+ 302.2, 0.92 min.

Workup

  1. customat room temperature
  2. customAfter quenched with water
  3. extractionthe reaction mixture was extracted with EtOAc
  4. washThe organic layers was washed with saturated NaHCO3 solution and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by automatic column chromatography (0 to 100% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-12996be1bd354b2580d003c8cd873a87
Source dataset
uspto-grants-2014_06
Patent number
US08748626B2

Reaction notes

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