Sodium → HCID 13371025, compound

HRID 1154306Notes

Reaction equation

HRID 1154306 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-f14988ebdc1e4c47bccfd991d2d4e0e8
Source dataset
uspto-grants-1984_12
Patent number
US04489077

Reaction notes

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