Methanol → HCID 58636771, compound

HRID 1158983Notes

Reaction equation

HRID 1158983 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6]([CH3:12])OC=2OCC)[CH2:3][CH2:2]1.[C:13]([O:21][CH3:22])(=[O:20])/[CH:14]=[CH:15]\[C:16]([O:18][CH3:19])=[O:17].[CH3:23][OH:24]>>[CH3:19][O:18][C:16]([C:15]1[C:4]([CH:1]2[CH2:2][CH2:3]2)=[N:5][C:6]([CH3:12])=[C:23]([OH:24])[C:14]=1[C:13]([O:21][CH3:22])=[O:20])=[O:17]

Participants

4

Reactant 3

HCID 887MethanolHCID 5271565Dimethyl maleateHCID 68644161HCID 68644161, compound

Product 1

HCID 58636771HCID 58636771, compoundYield 66%

Conditions

Temperature
0 °C

Procedure

2-Cyclopropyl-5-ethoxy-4-methyl-oxazole (164) (33.8 g, 0202 mmol) in neat dimethyl maleate (115.8 g, 807 mmol) was refluxed for 4 hours. The reaction was cooled to 0° C., added anhydrous methyl alcohol (500 mL) and bubbled hydrogen chloride gas into the suspension for 15 minutes. The reaction flask was sealed with a rubber septum and kept in a fridge for overnight. The solid was filtered off and washed with methanol and diethyl ether. The filtrate was evaporated to give 2-cyclopropyl-5-hydroxy-6-methyl-pyridine-3,4-dicarboxylic acid dimethyl ester (165) (35.2 g, 66% yield) as a colorless solids.

Workup

  1. custombubbled hydrogen chloride gas into the suspension for 15 minutes
  2. customThe reaction flask was sealed with a rubber septum
  3. filtrationThe solid was filtered off
  4. washwashed with methanol and diethyl ether
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-f088b2b84f014b26863df0b98aebacbe
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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