Lithium borohydride → [4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-methanol

HRID 854518Notes

Reaction equation

HRID 854518 reaction equation
C[O:2][C:3]([C:5]1[O:9][C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:7][C:6]=1[CH2:20][CH3:21])=O.[Li+].[BH4-]>C1COCC1>[CH2:20]([C:6]1[N:7]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[O:9][C:5]=1[CH2:3][OH:2])[CH3:21]

Participants

4

Reactant 2

HCID 4148881Lithium borohydride2×HCID 587658204-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carboxylic acid methyl ester

Product 1

HCID 58765785[4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carboxylic acid methyl ester (4.63 g, 15.47 mmole) in THF (100 mL), is added LiBH4 in one portion at 0° C. The reaction is warmed up to room temperature and stirred for an hour. Additional LiBH4 is added and the reaction is heated at 60° C. for 30 minutes. The excess amount of LiBH4 is destroyed using 6N HCl (50 mL) dropwise at 0° C. The mixture is partitioned between ethyl acetate (300 mL) and brine (300 mL). The organic layer is washed with brine (3×300 mL), dried over Na2SO4, filtered and concentrated. The crude product is purified by flash chromatography, eluting with 60% ethyl acetate in hexane and concentrated to provide the titled compound as a white solid. Mass [EI+] 272 (M+H)+.

Workup

  1. temperaturethe reaction is heated at 60° C. for 30 minutes
  2. customThe excess amount of LiBH4 is destroyed
  3. customdropwise at 0° C
  4. customThe mixture is partitioned between ethyl acetate (300 mL) and brine (300 mL)
  5. washThe organic layer is washed with brine (3×300 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product is purified by flash chromatography
  10. washeluting with 60% ethyl acetate in hexane
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-394bfb558d1544a098e5f7f449a3d794
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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