Water → HCID 57736326, compound

HRID 2261359Notes

Reaction equation

HRID 2261359 reaction equation
[CH3:1][C:2]([C:8]1[O:12][N:11]=[C:10]([C:13](OCC)=[O:14])[CH:9]=1)([O:4][CH2:5][C:6]#[CH:7])[CH3:3].[BH4-].[Na+].O>C(O)C>[CH3:3][C:2]([C:8]1[O:12][N:11]=[C:10]([CH2:13][OH:14])[CH:9]=1)([O:4][CH2:5][C:6]#[CH:7])[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 57736353HCID 57736353, compound

Product 1

HCID 57736326HCID 57736326, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.25 g of ethyl 5-[1-methyl-1-(2-propynyloxy)ethyl]isoxazole-3-carboxylate was dissolved in 2 ml of ethanol, and 0.1 g of sodium borohydride was then added. The mixture was stirred at room temperature for 5 hours. After 20 ml of water was added, the reaction mixture 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 0.20 g of {5-[1-methyl-1-(2-propynyloxy)ethyl]isoxazol-3-yl}methanol.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-853e9efc2803403d964bec3a6ee8f796
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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