Methyl iodide → HCID 12486321, compound

HRID 864764Notes

Reaction equation

HRID 864764 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8]CC(O)CO)=[CH:3][CH:2]=1.[CH3:14][C:15](C)([O-:17])[CH3:16].[K+].I[CH3:21].C1C[O:25][CH2:24]C1>>[CH2:7]([O:8][CH2:14][CH:15]([O:17][CH3:21])[CH2:16][O:25][CH3:24])[C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 8028Tetrahydrofuran2×HCID 980723-(Benzyloxy)-1,2-propanediolHCID 23665647Potassium tert-butoxide

Product 1

HCID 12486321HCID 12486321, compound

Procedure

A solution of 10.0 g (0.055 mol) of DL-α-O-benzylglycerol in a little THF was added to a suspension of 15.38 g (0.137 mol) of potassium tert-butoxide in 300 mL of THF. The mixture was stirred for 1 hr at RT and 18.72 (0.132 mol) of iodomethane was added. A white solid immediately separated. The reaction was stirred for 10 hr at RT, cooled, carefully diluted with sodium chloride solution and extracted with ether. The organic layer was washed with water, 5% HCl, water and saturated NaCl and dried. The solvent was removed and the residue was purified by flash chromatography to give 1-benzyloxy-2,3-dimethoxypropane, 9.16 g (79%), as an oil.

Workup

  1. customA white solid immediately separated
  2. stirringThe reaction was stirred for 10 hr at RT
  3. temperaturecooled
  4. additioncarefully diluted with sodium chloride solution
  5. extractionextracted with ether
  6. washThe organic layer was washed with water, 5% HCl, water and saturated NaCl
  7. customdried
  8. customThe solvent was removed
  9. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-005731aa66f345bfb8a7bcdba8c39049
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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