Hydrogen Peroxide → [5-(Methoxymethyl)-1,2-oxazol-3-yl]methanol

HRID 54419Notes

Reaction equation

HRID 54419 reaction equation
C(=CCO[C:6]1[CH:10]=[C:9]([CH2:11][O:12][CH3:13])[O:8][N:7]=1)=O.[CH3:14]CC(C)[BH-](C(C)CC)C(C)CC.[Li+].[OH-:28].[Na+].OO>O1CCCC1.C(O)C.O>[OH:28][CH2:14][C:6]1[CH:10]=[C:9]([CH2:11][O:12][CH3:13])[O:8][N:7]=1

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 199587883-Carbonylethoxy-5-methoxymethyl-isoxazole

Product 1

HCID 19958730[5-(Methoxymethyl)-1,2-oxazol-3-yl]methanol

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6.55 g of 3-carbonylethoxy-5-methoxymethyl-isoxazole in 70 ml dry tetrahydrofuran were added 77.6 ml of a 1 N solution of L-selectride® at 0° C. The solution was stirred overnight at room temperature. After cooling to 0° C. 13 ml of water and 33 ml of ethanol were added, then simultaneously 33 ml of a 6 N solution of sodium hydroxide and 49 ml hydrogen peroxide were added with caution. After stirring for half an hour the supernatant was decanted, the residue washed several times with methylene chloride. The aqueous phase was extracted with dichloromethane in an extraction apparatus for one day. The organic phase was dried over sodium sulfate and the solvent evaporated to give 4.1 g product.

Workup

  1. temperatureAfter cooling to 0° C
  2. stirringAfter stirring for half an hour the supernatant
  3. customwas decanted
  4. washthe residue washed several times with methylene chloride
  5. extractionThe aqueous phase was extracted with dichloromethane in an extraction apparatus for one day
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-786793f924a748b88eb7d99d760a55c7
Source dataset
uspto-grants-1997_04
Patent number
US05622953

Reaction notes

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