Hydrochloric Acid → HCID 22261992, compound

HRID 1610689Notes

Reaction equation

HRID 1610689 reaction equation
[F:1][C:2]([F:16])([O:6][C:7]1[CH:11]=[C:10]([C:12](OC)=[O:13])[O:9][N:8]=1)[CH:3]([F:5])[F:4].[BH4-].[Na+].Cl>CO>[F:16][C:2]([F:1])([O:6][C:7]1[CH:11]=[C:10]([CH2:12][OH:13])[O:9][N:8]=1)[CH:3]([F:4])[F:5]

Participants

5

Procedure

To a solution of methyl 3-(1,1,2,2-tetrafluoroethoxy)-5-isoxazole carboxylate (1.975 g, 8.124 mmol) in methanol (30 ml) was added sodium borohydride (0.40 g, 10.6 mmol) by small portions under ice-cooling, and the mixture was stirred overnight at room temperature. To the reaction solution was added dilute hydrochloric acid, the mixture was stirred at room temperature for 1 hr and washed three times with ethyl acetate. The recovered organic layer was dried over anhydrous magnesium sulfate, and passed through silica gel. The solvent was evaporated under reduced pressure to give a crude product of [3-(1,1,2,2-tetrafluoroethoxy)isoxazol-5-yl]methanol as a yellow liquid (1.72 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. washwashed three times with ethyl acetate
  4. dry with materialThe recovered organic layer was dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3d55bf8d604145c99123d0fcf52035fc
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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