Methyl iodide → HCID 13559545, compound

HRID 638623Notes

Reaction equation

HRID 638623 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]1[C@@H:14]([CH2:15][C:16]([OH:18])=[O:17])[CH:13]=[CH:12][C@@H:11]1[OH:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH2:1]([O:8][CH2:9][C@@H:10]1[C@@H:14]([CH2:15][C:16]([O:18][CH3:20])=[O:17])[CH:13]=[CH:12][C@@H:11]1[OH:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 13559543HCID 13559543, compound

Product 1

HCID 13559545HCID 13559545, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 23.6 g of (1S,2S,3S)-2-benzyloxymethyl-3-carboxymethyl-4-cyclopenten-1-ol [the compound described in J. Am. Chem. Soc., 93, 1492 (1971)] in 200 ml of acetone, 27.6 g of potassium carbonate and 11.36 g of methyl iodide were added. The mixture was stirred for 50 min at room temperature, and then refluxed for 2 hrs. After reacting, the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (2:1) as eluent to give 24.9 g of the title compound having the following physical characteristics, in a 99% yield.

Workup

  1. temperaturerefluxed for 2 hrs
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel using
  5. additiona mixture of cyclohexane and ethyl acetate (2:1) as eluent

Sources & evidence

ORD record
ord-a416d62aff4c4ec38899826476f2f796
Source dataset
uspto-grants-1985_12
Patent number
US04562207

Reaction notes

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