Methyl iodide → HCID 67715083, compound

HRID 2400120Notes

Reaction equation

HRID 2400120 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:5]([CH2:19][C:20]([O:22][CH2:23]C)=[O:21])=[CH:4][N:3]=1.[H-].[Na+].CI.[CH:29]([O:31][CH3:32])=O>CCOCC>[CH3:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[CH:10]=2)[C:5]([C:19](=[CH:29][O:31][CH3:32])[C:20]([O:22][CH3:23])=[O:21])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 7865Methyl formateHCID 24758Sodium hydrideHCID 19044668HCID 19044668, compound

Product 1

HCID 67715083HCID 67715083, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl α-[2-methyl-4-(3-trifluoromethylphenoxy)-5-pyrimidinyl]-acetate (3 g, 8 mmol) are dissolved in methyl formate (10 ml) and added to a suspension of NaH (0.6 g, 80% in oil, 20 mmol) in 1,2-dimethoxyaethane at room temperature. After 16 hours methyl iodide (2.5 ml, 40 mmol) is added with cooling. After further 2 hours the reaction mixture is diluted with ether and washed with brine. Drying and chromatography on silicagel (eluant: hexane/ethyl acetate 1:1) gives the methyl α-[2-methyl-4-(3-trifluoromethylphenoxy)-5-pyrimidinyl]-β-methoxyacrylate compound as a crystalline solid, m.p. 100°-102° C.

Workup

  1. temperaturewith cooling
  2. washwashed with brine
  3. customDrying

Sources & evidence

ORD record
ord-62f9a0e81d1842ffa5bfb12a56788b5c
Source dataset
uspto-grants-1995_09
Patent number
US05453427

Reaction notes

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