Sodium Hydroxide → 5-Isoxazolemethanol,3-(trifluoromethyl)-(9CI)

HRID 1025971Notes

Reaction equation

HRID 1025971 reaction equation
Cl.[NH2:2][OH:3].[OH-].[Na+].[Si]([O:13][CH2:14][C:15]#[C:16][C:17](=O)[C:18]([F:21])([F:20])[F:19])(C(C)(C)C)(C)C>CO>[F:19][C:18]([F:21])([F:20])[C:17]1[CH:16]=[C:15]([CH2:14][OH:13])[O:3][N:2]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 86663139HCID 86663139, compound

Product 1

HCID 133079935-Isoxazolemethanol,3-(trifluoromethyl)-(9CI)Yield 31.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of hydroxylamine hydrochloride (0.694 g 0.010 mol, 1 equ) and 0.02 g sodium hydroxide in 25 mL methanol was added 5-(tert-butyldimethylsilyloxy)-1,1,1-trifluoropent-3-yn-2-one (2.66 g 0.010 mol, 1 equ) and the mixture was heated to reflux for 3 h. The reaction mixture was extracted with ethyl acetate and purified by chromatography on silica gel (50 g) using a gradient of heptane:ethyl acetate=9:1 to 1:1. to yield 0.524 g of the title compound as colorless oil, MS 167(M)+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 h
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. custompurified by chromatography on silica gel (50 g)

Sources & evidence

ORD record
ord-734792f86e0e4bed86ecac59b8bb46cc
Source dataset
uspto-grants-2014_05
Patent number
US08729105B2

Reaction notes

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