Methyl iodide → 2-O-Methyl-1,3-O,O-benzylideneglycerol

HRID 1197157Notes

Reaction equation

HRID 1197157 reaction equation
[Na].[C:2]1([CH:8]2[O:13][CH2:12][CH:11]([OH:14])[CH2:10][O:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:17]I>CN(C)C=O.ClCCl>[C:2]1([CH:8]2[O:13][CH2:12][CH:11]([O:14][CH3:17])[CH2:10][O:9]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 743621,3-Dioxan-5-ol, 2-phenyl-HCID 5360545Sodium

Product 1

HCID 1285142-O-Methyl-1,3-O,O-benzylideneglycerolYield 75%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

10 g of the sodium salt of 1b, obtained by reaction with sodium hydride in dimethylformamide, was treated with 16 g of methyl iodide. The mixture was stirred at 50° C. for 5 hours, and the dimethylformamide was eliminated in vacuo. The residue was dissolved in dichloromethane, washed and dried. The solvent was evaporated off and the product was chromatographed on silica gel (eluent : dichloromethane) to give 2b.

Workup

  1. washwashed
  2. customdried
  3. customThe solvent was evaporated off
  4. customthe product was chromatographed on silica gel (eluent : dichloromethane)

Sources & evidence

ORD record
ord-4eae467844f5405780d57ed7f81df576
Source dataset
uspto-grants-1992_05
Patent number
US05116992

Reaction notes

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