Methyl iodide → 2-methoxymethyl-3-benzyloxy-6-methyl-pyran-4(1H)-one

HRID 1279402Notes

Reaction equation

HRID 1279402 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]1[O:6][C:7]([CH3:20])=[CH:8][C:9](=[O:19])[C:10]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.I[CH3:22]>CN(C=O)C>[CH3:22][O:3][CH2:4][C:5]1[O:6][C:7]([CH3:20])=[CH:8][C:9](=[O:19])[C:10]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 111394092-hydroxymethyl-3-benzyloxy-6-methyl-pyran-4(1H)-one

Product 1

HCID 117473362-methoxymethyl-3-benzyloxy-6-methyl-pyran-4(1H)-oneYield 90.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (0.48 g, 20 mmol, 2 eq.) in 30 ml dry DMF was added 2-hydroxymethyl-3-benzyloxy-6-methyl-pyran-4(1H)-one (2.46 g, 10 mmol, 1 eq.) followed by dropwise addition of iodomethane (4.26 g, 30 mmol, 3 eq.) at 0° C. under nitrogen. After stiming for 30 minutes at this temperature, the reaction mixture was poured into ice cold water (100 ml) and extracted with dichloromethane (3×50 ml). The combined organic fractions were dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to yield the crude product (2.6 g,˜100%) as an orange oil which solidified on cooling. Recrystallisation from CH2Cl2/Pet. ether 40/60 afforded the pure product (2.35 g, 90%) as a white crystalline solid. m.p. 30-32° C.

Workup

  1. extractionextracted with dichloromethane (3×50 ml)
  2. dry with materialThe combined organic fractions were dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto yield the crude product (2.6 g,˜100%) as an orange oil which
  6. temperatureon cooling
  7. customRecrystallisation from CH2Cl2/Pet. ether 40/60

Sources & evidence

ORD record
ord-1b159c67401e473d92d79fa9103262e3
Source dataset
uspto-grants-2002_09
Patent number
US06448273B1

Reaction notes

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