Oxazole → Ethyl 2-(4'-hydroxyphenyl)-1,3-oxazole-4-carboxylate

HRID 378746Notes

Reaction equation

HRID 378746 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.Br[CH2:12][C:13](=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15].O1C=CN=C1>C(OCC)(=O)C>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[O:7][CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9255OxazoleHCID 650524-HydroxybenzamideHCID 66144Ethyl bromopyruvate

Product 1

HCID 2758854Ethyl 2-(4'-hydroxyphenyl)-1,3-oxazole-4-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 25.0 g (182.3 mmol) of 4-hydroxybenzamide and 23.0 mL (182.3 mmol) of ethyl bromopyruvate was stirred and heated at 115° C. for 30 minutes. The mixture cooled to room temperature and sat under N2 atmosphere overnight. Ethyl acetate (100 mL) was added and the mixture stirred for 1 hour. The solid oxazole (36.99 g, 158.6 mmol) was collected by suction filtration in 87% yield: 1H NMR (CDCl3) δ10.21 (broad s, 1H), 8.82 (s, 1H), 7.83 (d, J=8.7 Hz, 2H), 6.90 (d, J=8.7 Hz, 2H), 4.29 (q, 2H), 1.29 (t, 3H); IR (cm-1) 3400, 3169, 1731, 1612, 1731, 1507, 1444; FDMS 233. Anal. (C12H11NO4) C, H, N.

Workup

  1. temperatureThe mixture cooled to room temperature
  2. stirringthe mixture stirred for 1 hour

Sources & evidence

ORD record
ord-2a70c776793a488e835bb49832b24ece
Source dataset
uspto-grants-2000_02
Patent number
US06031095

Reaction notes

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