Hydroxyamine hydrochloride → 3-(1,2-Oxazol-5-yl)phenol

HRID 1272191Notes

Reaction equation

HRID 1272191 reaction equation
C[N:2](C)[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=1)=[O:6].Cl.NO>O1CCOCC1.O>[O:6]1[C:5]([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 69517765HCID 69517765, compound

Product 1

HCID 227234713-(1,2-Oxazol-5-yl)phenolYield 75.5%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A solution of 3-(dimethylamino)-1-(3-hydroxyphenyl)-2-propen-1-one (2.2 g, 11.5 mmol) and hydroxylamine hydrochloride (1.17 g, 16.8 mmol) in 45 ml dioxane/water 1:1 is heated for 2 hours at 60° C. The reaction is poured into ice-water and the precipitate is collected by filtration, washed with water, and dried in vacuo to give 1.4 g of 3-(5-isoxazolyl)phenol (75.5%). This phenolic product is reacted with (2S)-glycidyl 3-nitrobenzenesulfonate substantially as described for Epoxide 1 to give 1.33 g of the title epoxide (70%).

Workup

  1. filtrationthe precipitate is collected by filtration
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-d03ab88a66ac4638bcf58c7ac02ee0f3
Source dataset
uspto-grants-2007_04
Patent number
US07208505B2

Reaction notes

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