Sodium → HCID 13371025, compound

HRID 1380410Notes

Reaction equation

HRID 1380410 reaction equation
I[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[CH:4]=1.[CH3:12][O-:13].[Na+].[Na]>CO.C1COCC1>[CH3:12][O:13][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[CH:4]=1

Participants

6

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 13371024HCID 13371024, compound

Product 1

HCID 13371025HCID 13371025, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.34 g (5 mmole) of methyl 5-(iodomethyl)-3-isoxazolecarboxylate in 20 ml of methanol and 5 ml of THF is added to a solution of methanol and 5 ml of THF is added to a solution of sodium methoxide prepared from 0.15 g (6.5 mmole) sodium and 10 ml of methanol. The reaction mixture is stirred at room temperature for four hours, heated to reflux for 30 minutes, and then worked up as usual giving 0.65 g of product. The crude ester is recrystallized from ether-cyclohexane mixture to give 0.33 g of off-white solid, mp 47.5°-49° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 minutes

Sources & evidence

ORD record
ord-af960b38e178410c9014fd213691e63f
Source dataset
uspto-grants-1986_04
Patent number
US04581458

Reaction notes

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