Water → HCID 90202510, compound

HRID 929765Notes

Reaction equation

HRID 929765 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:18]=[C:17]([C:19]([NH2:21])=[O:20])[O:16][N:15]=2)=[CH:10][CH:9]=1)(C)(C)C.N1C=CC=CC=1.O>C1COCC1>[OH:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:18]=[C:17]([C:19]([NH2:21])=[O:20])[O:16][N:15]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 131735126HCID 131735126, compound2×

Product 1

HCID 90202510HCID 90202510, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 3-[4-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-isoxazole-5-carboxylic acid amide (which may be prepared as described in Preparation of Intermediate 18; 800 mg, 2.4 mmol) in THF (8 mL) and HF/pyridine (70%; 0.25 mL) was stirred at room temperature. After 30 min, an addition portion of THF (8 mL) was added and the mixture was stirred for 5 h. H2O was added and the mixture was extracted four times with CHCl3/CH3OH (7:3). The organic layers were dried (Na2SO4), filtered and evaporated to give 3-(4-hydroxymethyl-phenyl)-isoxazole-5-carboxylic acid amide (300 mg, 57%).

Workup

  1. stirringthe mixture was stirred for 5 h
  2. extractionthe mixture was extracted four times with CHCl3/CH3OH (7:3)
  3. dry with materialThe organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-45a6a52f104a48f397da94a613197edc
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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