Water → {5-[1-(t-Butyldimethylsilanyloxy)ethyl]isoxazol-3-yl}methanol

HRID 2261346Notes

Reaction equation

HRID 2261346 reaction equation
[Si:1]([O:8][CH:9]([C:11]1[O:15][N:14]=[C:13]([C:16](OCC)=[O:17])[CH:12]=1)[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+].O>C(O)C>[Si:1]([O:8][CH:9]([C:11]1[O:15][N:14]=[C:13]([CH2:16][OH:17])[CH:12]=1)[CH3:10])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 57736274Ethyl 5-[1-(t-butyldimethylsilanyloxy)ethyl]isoxazole-3-carboxylate

Product 1

HCID 57736294{5-[1-(t-Butyldimethylsilanyloxy)ethyl]isoxazol-3-yl}methanolYield 95.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8.95 g of ethyl 5-[1-(t-butyldimethylsilanyloxy)ethyl]isoxazole-3-carboxylate was dissolved in 60 ml of ethanol, and 2.30 g of sodium borohydride was then added. The mixture was stirred at room temperature for 4 hours. After 30 ml of water was added, the reaction mixture was concentrated to 30 ml under reduced pressure. The concentrated solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 7.35 g of {5-[1-(t-butyldimethylsilanyloxy)ethyl]isoxazol-3-yl}methanol.

Workup

  1. concentrationthe reaction mixture was concentrated to 30 ml under reduced pressure
  2. extractionThe concentrated solution was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c910b732c9ec4679a2344a8f943137d9
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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