Acetone → HCID 10942644, compound

HRID 1464753Notes

Reaction equation

HRID 1464753 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:14][C:15]([CH3:17])=[O:16]>>[S:1]1[CH:5]=[CH:4][C:3](/[CH:6]=[CH:14]/[C:15](=[O:16])[CH3:17])=[CH:2]1

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 681353-Thiophenecarboxaldehyde

Product 1

HCID 10942644HCID 10942644, compound

Procedure

1.6 g of 3-thiophenecarboxaldehyde was dissolved in 30 ml of acetone, and 20 g of potassium carbonate was added. The mixture was stirred overnight at room temperature. The solvent was evaporated, and the residue was worked up in a customary manner. The resulting alcohol compound was dissolved in 10 ml of methylene chloride, and 1.1 ml of methanesulfonyl chloride and 2.3 ml of triethylamine were added. The mixture was stirred overnight at room temperature, and then the solvent was evaporated. The residue was worked up in a customary manner, and purified by silica gel column chromatography [hexane/ethyl acetate=40/1] to give 650 mg of the captioned compound as a pale yellow oil.

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe resulting alcohol compound was dissolved in 10 ml of methylene chloride
  3. addition1.1 ml of methanesulfonyl chloride and 2.3 ml of triethylamine were added
  4. stirringThe mixture was stirred overnight at room temperature
  5. customthe solvent was evaporated
  6. custompurified by silica gel column chromatography [hexane/ethyl acetate=40/1]

Sources & evidence

ORD record
ord-3826336d252e47908f67e86feccb2c01
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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