Ethyl Acetate → HCID 59594774, compound

HRID 2263372Notes

Reaction equation

HRID 2263372 reaction equation
[F:1][C:2]([F:25])([F:24])[CH2:3][O:4][CH2:5][C:6]1[N:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[O:9][C:10]=1[C:11](O)=[O:12].C(OCC)(=O)C>O1CCCC1>[F:25][C:2]([F:1])([F:24])[CH2:3][O:4][CH2:5][C:6]1[N:7]=[C:8]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:19]=2)[O:9][C:10]=1[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 59594738HCID 59594738, compound

Product 1

HCID 59594774HCID 59594774, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

1.0 g 4-(2,2,2-Trifluoro-ethoxymethyl)-2-(4-trifluoromethyl-phenyl)-oxazole-5-carboxylic acid were dissolved in 30 ml tetrahydrofuran. At 0-5° C. 6.6 ml of a one molar solution of borane tetrahydrofuran complex were added. The reaction mixture was stirred at room temperature for three hours and at 60° C. for one hour. The cooled reaction mixture was diluted by addition of 100 ml ethyl acetate and washed with 50 ml water. The organic phase was dried over MgSO4 then the solvent was removed in vacuo. The residue was purified by RP-HPLC to obtain 422 mg [4-(2,2,2-trifluoro-ethoxymethyl)-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-methanol.

Workup

  1. customAt 0-5° C
  2. customThe cooled reaction mixture
  3. washwashed with 50 ml water
  4. dry with materialThe organic phase was dried over MgSO4
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-9fd09028079744c192fb1c1be7b243c7
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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