Methyl iodide → HCID 23572096, compound

HRID 1824571Notes

Reaction equation

HRID 1824571 reaction equation
[OH:1][CH2:2][C:3](=[CH2:14])[C:4]([O:6][C:7]1([CH2:12][CH3:13])[CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:5].[CH3:15]I>[Ag-]=O.CN(C)C=O>[CH3:15][O:1][CH2:2][C:3](=[CH2:14])[C:4]([O:6][C:7]1([CH2:12][CH3:13])[CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:5]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 17861479HCID 17861479, compound

Product 1

HCID 23572096HCID 23572096, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 19.8 g of 1-ethylcyclopentyl α-(hydroxymethyl)acrylate, 40.0 g of methyl iodide, 30.0 g of silver (I) oxide and 50 g of N,N-dimethylformamide was stirred at 50° C. for 30 hours. The solids were filtered off, followed by conventional aqueous workup. The solvent was distilled off in vacuo. Purification by distillation (boiling point 53° C./16 Pa) gave 1-ethylcyclopentyl α-(methoxymethyl)acrylate represented by formula (10). The yield was 62%.

Workup

  1. filtrationThe solids were filtered off
  2. distillationThe solvent was distilled off in vacuo
  3. customPurification
  4. distillationby distillation (boiling point 53° C./16 Pa)

Sources & evidence

ORD record
ord-12473d4ae47a4423ac4261091fced7be
Source dataset
uspto-grants-2006_05
Patent number
US07041846B2

Reaction notes

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