Sodium borohydride → (5-(Furan-2-yl)-1,2-oxazol-3-yl)methanol

HRID 606283Notes

Reaction equation

HRID 606283 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[O:8][N:7]=1)=O)C.[BH4-].[Na+]>C(O)C>[O:12]1[CH:13]=[CH:14][CH:15]=[C:11]1[C:9]1[O:8][N:7]=[C:6]([CH2:4][OH:3])[CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 7127810Ethyl 5-(2-furyl)isoxazole-3-carboxylate

Product 1

HCID 7164591(5-(Furan-2-yl)-1,2-oxazol-3-yl)methanolYield 88.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2.00 g of 5-furan-2-yl-isoxazole-3-carboxylic acid ethyl ester in absolute ethanol was slowly added 548 mg of sodiumborohydride at 0° C. After stirring at room temperature for 4 hrs, the reaction was quenched by addition of distilled water. The reaction solution was concentrated under reduced pressure and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to produce 1.41 g of (5-furan-2-yl-isoxazol-3-yl)-methanol. (Yield 88%). This concentrate was used in the next step without further purification.

Workup

  1. customat 0° C
  2. customthe reaction was quenched by addition of distilled water
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1cea36d8160c42ebaa3d9a4b5165e8e6
Source dataset
uspto-grants-2011_03
Patent number
US07915297B2

Reaction notes

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