Water → (5-Tert-butyl-1,2-oxazol-3-yl)methanol

HRID 2261291Notes

Reaction equation

HRID 2261291 reaction equation
[C:1]([C:5]1(C(OCC)=O)[O:9][NH:8][CH:7]=[CH:6]1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O.[O:18]1CCC[CH2:19]1>C(O)C>[C:1]([C:5]1[O:9][N:8]=[C:7]([CH2:19][OH:18])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 68779846Ethyl 5-t-butyl-isoxazole-5-carboxylate

Product 1

HCID 10820794(5-Tert-butyl-1,2-oxazol-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.83 g of ethyl 5-t-butyl-isoxazole-5-carboxylate was dissolved in 18 ml of tetrahydrofuran, and 0.70 g of sodium borohydride in 10 ml of ethanol was then added. The mixture was stirred at room temperature for 10 hours. After 5 ml of water was added, the reaction mixture was concentrated to 5 ml under reduced pressure. The concentrated solution was extracted with methyl-t-butyl ether. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 0.62 g of (5-t-butyl-isoxazol-3-yl)methanol.

Workup

  1. concentrationthe reaction mixture was concentrated to 5 ml under reduced pressure
  2. extractionThe concentrated solution was extracted with methyl-t-butyl ether
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fdd8deec2e8049fd89820f13d8cb5205
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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