Triethyl orthoacetate → Methyl 4-(2-methyl-1,3-oxazol-5-yl)-3,5-dimethoxybenzoate

HRID 1096989Notes

Reaction equation

HRID 1096989 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[C:15]([O:16][CH3:17])=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[O:18][CH3:19])=[O:5].[C:20](OCC)(OCC)(OCC)[CH3:21]>>[CH3:20][C:21]1[O:5][C:4]([C:6]2[C:7]([O:18][CH3:19])=[CH:8][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:14][C:15]=2[O:16][CH3:17])=[CH:3][N:2]=1

Participants

3

Reactant 2

HCID 66221Triethyl orthoacetateHCID 66782707Methyl 4-(aminoacetyl)-3,5-dimethoxybenzoate hydrochloride

Product 1

HCID 57930976Methyl 4-(2-methyl-1,3-oxazol-5-yl)-3,5-dimethoxybenzoate

Conditions

Temperature
140 °C

Procedure

Methyl 4-(aminoacetyl)-3,5-dimethoxybenzoate hydrochloride was dissolved in triethyl orthoacetate, paratoluenesulfonic acid monohydrate (10 mg) was added to it, and stirred at 140° C. for 6 hours. The reaction liquid was cooled to room temperature, then triethyl orthoacetate was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (hexane/ethyl acetate=100/0 to 30/70) to obtain the title compound.

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. customtriethyl orthoacetate was evaporated away under reduced pressure
  4. customthe residue was purified through silica gel column chromatography (hexane/ethyl acetate=100/0 to 30/70)

Sources & evidence

ORD record
ord-01dc5985ce724fab93919cb95bc03515
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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