Methyl iodide → Methyl 7-(4-hydroxycyclopent-2-en-1-on-2-yl)-5-heptynoate

HRID 1032506Notes

Reaction equation

HRID 1032506 reaction equation
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][C:9]#[C:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:3]1.[C:17](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][C:9]#[C:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 147744257-(4-Hydroxycyclopent-2-en-1-on-2-yl)-5-heptynoic acid

Product 1

HCID 14656225Methyl 7-(4-hydroxycyclopent-2-en-1-on-2-yl)-5-heptynoateYield 81.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 5.8 g of 7-(4-hydroxycyclopent-2-en-1-on-2-yl)-5-heptynoic acid, 3.95 g of potassium carbonate, 7.4 g of iodomethane and 52 ml of acetone was refluxed for 2.5 hours. Most of the acetone was evaporated and the residue was partitioned with water and ether. The ether layer was separated, washed with brine, dried and concentrated, giving 5.02 g of the desired compound as an oil; PMR δ 3.72 (3H, s, methyl ester).

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. customMost of the acetone was evaporated
  3. customthe residue was partitioned with water and ether
  4. customThe ether layer was separated
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-24863c94644649c4bc1e57ddfd25ad83
Source dataset
uspto-grants-1990_09
Patent number
US04958037

Reaction notes

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