Ethanol → 2,3-Dihydro-2-(methylthio)-1H-inden-1-one

HRID 1859382Notes

Reaction equation

HRID 1859382 reaction equation
Br[CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:11].C(O)C.[Na].[CH3:16][SH:17]>CCOCC.O>[CH3:16][S:17][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:11]

Participants

7

Reactant 4

HCID 702EthanolHCID 878MethanethiolHCID 1372032-Bromo-1-indanoneHCID 5360545Sodium

Product 1

HCID 120675262,3-Dihydro-2-(methylthio)-1H-inden-1-oneYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

After 10 g of 2-bromo-1-indanone was dissolved into 50 ml of ethanol, 25 ml of a 15% aqueous solution of a sodium salt of methylmercaptan was added dropwise thereto. After stirring for 3 hours at room temperature, the reaction mixture was poured into 300 ml of cold water. After 200 ml of ether was added thereto for extracting an organic phase, the ether layer was sequentially washed with an aqueous sodium chloride solution and water. After the ether layer was dried with magnesium sulfate, the ether was evaporated under vacuum. The residue was isolated and purified through a silica gel column (elute: hexane/ethyl acetate=7/1) to provide 3.2 g of 2-(methylthio)-1-indanone (yield: 38%).

Workup

  1. additionwas added dropwise
  2. extractionfor extracting an organic phase
  3. washthe ether layer was sequentially washed with an aqueous sodium chloride solution and water
  4. dry with materialAfter the ether layer was dried with magnesium sulfate
  5. customthe ether was evaporated under vacuum
  6. customThe residue was isolated
  7. custompurified through a silica gel column (elute: hexane/ethyl acetate=7/1)

Sources & evidence

ORD record
ord-b878b5739a1e4e8fa4df84e34c6711a4
Source dataset
uspto-grants-2003_03
Patent number
US06528232B1

Reaction notes

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