Methyl iodide → HCID 55275333, compound

HRID 1386789Notes

Reaction equation

HRID 1386789 reaction equation
IC.[C:3]([O-:6])([O-])=O.[K+].[K+].[CH2:9]([C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[C:13]=1O)[CH:10]=[CH2:11]>CC(C)=O.O>[CH2:9]([C:12]1[CH:13]=[C:14]([F:19])[CH:15]=[C:16]([F:18])[C:17]=1[O:6][CH3:3])[CH:10]=[CH2:11]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21180843HCID 21180843, compound

Product 1

HCID 55275333HCID 55275333, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of iodomethane (1.8 mL, 29.4 mmol), K2CO3 (2.4 grams, 17.6 mmol) and 2-Allyl-4,6-difluorophenol (1.0 grams, 5.9 mmol) in 20 mL acetone was refluxed overnight. The mixture was diluted with water and extracted with EtOAc. The organic layer was dried over sodium sulfate and concentrated. Flash chromatography (Hexane) afforded 0.67 g (63%) of the title compound. 1H NMR (400 MHz, CDCl3). S 3.36 (d, 21), 3.82 (s, 3H), 4.97-5.12 (m, 2H), 5.85-6.0 (m, 1H), 6.4-6.5 (m, 2H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1309ea29f9e54ada9891d1134dd49092
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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