Methyl iodide → HCID 131724375, compound

HRID 49332Notes

Reaction equation

HRID 49332 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:29]=[CH:30][C:31]=1[CH2:32][O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[O:13][CH2:14][C:15]1[S:19][C:18](/[C:20](/[CH2:27][CH3:28])=[CH:21]/[CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:17][CH:16]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:41](=O)([O-])[O-].[K+].[K+].IC>CC(=O)CC>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:29]=[CH:30][C:31]=1[CH2:32][O:33][Si:34]([C:37]([CH3:39])([CH3:38])[CH3:40])([CH3:35])[CH3:36])[O:13][CH2:14][C:15]1[S:19][C:18](/[C:20](/[CH2:27][CH3:28])=[CH:21]/[CH2:22][CH2:23][C:24]([O:26][CH3:41])=[O:25])=[CH:17][CH:16]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 69825580(e)-5-{5-[3,4-Bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-2-thienyl}-4-heptenoic acid

Product 1

HCID 131724375HCID 131724375, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

4.3 g (7.1 mmol) of (E)-5-{5-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-2-thienyl}-4-heptenoic acid are dissolved in 70 mL of 2-butanone, and 1.1 g of potassium carbonate (7.8 mmol) and 2.2 mL of iodomethane (35 mmol) are added. The medium is refluxed for 12 hours, cooled and filtered. The filtrate is concentrated under reduced pressure and then purified by chromatography on a column of silica. A yellow oil is obtained (m=4.34 g; Y=98%).

Workup

  1. temperatureThe medium is refluxed for 12 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. custompurified by chromatography on a column of silica
  6. customA yellow oil is obtained (m=4.34 g; Y=98%)

Sources & evidence

ORD record
ord-b0502686c84e4465bd9abdd4ae24eb3d
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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