Methyl iodide → HCID 19809538, compound

HRID 374206Notes

Reaction equation

HRID 374206 reaction equation
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([OH:16])=[S:15])=[CH:3]1.[C:23](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:14]([O:16][CH3:23])=[S:15])=[CH:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178516562HCID 178516562, compound

Product 1

HCID 19809538HCID 19809538, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 4.38 g. of 7-(4-hydroxycyclopent-2-en-1-on-2-yl)-2-phenylthioheptanoic acid, 1.99 g. of potassium carbonate, 1.63 ml. of iodomethane and 26 ml. of acetone is refluxed for 3.5 hours. The acetone is evaporated and the residue is partitioned between water and ether. The ether layer is washed with brine, dried and concentrated, giving the product as an oily liquid, identified by PMRδ 3.67 (3, s).

Workup

  1. additionA stirred mixture of 4.38 g
  2. customThe acetone is evaporated
  3. customthe residue is partitioned between water and ether
  4. washThe ether layer is washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4c16224c3b4e439c9d9e7effda4fc331
Source dataset
uspto-grants-1992_11
Patent number
US05166369

Reaction notes

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