Water → HCID 57736305, compound

HRID 2261342Notes

Reaction equation

HRID 2261342 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([C:15](OCC)=[O:16])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+].O>C(O)C>[Si:1]([O:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([CH2:15][OH:16])[CH:11]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 59463439HCID 59463439, compound

Product 1

HCID 57736305HCID 57736305, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

23.82 g of ethyl 5-(t-butyldimethylsilanyloxymethyl)-isoxazole-3-carboxylate was dissolved in 100 ml of ethanol, and 3.16 g of sodium borohydride was then added. The mixture was stirred at room temperature for 4 hours. After 50 ml of water was added, the reaction mixture was concentrated to 50 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 18.74 g of [5-(t-butyldimethylsilanyloxymethyl)isoxazol-3-yl]methanol.

Workup

  1. concentrationthe reaction mixture was concentrated to 50 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-a61e032d3a514aa1bf5f49aee8727316
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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