Methyl iodide → HCID 23119079, compound

HRID 1819508Notes

Reaction equation

HRID 1819508 reaction equation
[F:1][C:2]1[C:7]([CH:8]([OH:14])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:6][CH:5]=[CH:4][C:3]=1[C:15]1([CH3:20])[O:19][CH2:18][CH2:17][O:16]1.[CH3:21]I.[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[F:1][C:2]1[C:7]([CH:8]([O:14][CH3:21])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:6][CH:5]=[CH:4][C:3]=1[C:15]1([CH3:20])[O:16][CH2:17][CH2:18][O:19]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 23119393HCID 23119393, compound

Product 1

HCID 23119079HCID 23119079, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF (35 mL) solution of 2-[2-fluoro-3-(1-hydroxyhexyl)phenyl]-2-methyl-1,3-dioxolane e (6.9 g) and methyl iodide (6.1 mL) was added sodium hydride (1.96 g) under ice-cooling. After the reaction mixture was stirred at room temperature for 1 h, a saturated ammonium chloride aqueous solution was added into the reaction mixture. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with water, and brine, dried over magnesium sulfate, and evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate=20:1) to obtain the compound (17) 6.99 g.

Workup

  1. temperaturecooling
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water, and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-0a576a89861e41c2859add60bb141ab2
Source dataset
uspto-grants-2009_10
Patent number
US07601746B2

Reaction notes

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