Water → HCID 44189333, compound

HRID 1949146Notes

Reaction equation

HRID 1949146 reaction equation
ClCCl.[Cl:4][C:5]1[CH:6]=[C:7]([CH:12]2[C:16]([OH:17])=[C:15]([C:18]([CH3:20])=[O:19])[CH:14]([CH3:21])[S:13]2)[CH:8]=[CH:9][C:10]=1[Cl:11].S(Cl)(Cl)(=O)=O.O>CCCCCC.C(OCC)(=O)C>[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2[S:13][C:14]([CH3:21])=[C:15]([C:18]([CH3:20])=[O:19])[C:16]=2[OH:17])[CH:8]=[CH:9][C:10]=1[Cl:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6344Dichloromethane2×HCID 24648Sulfuryl chlorideHCID 58281528HCID 58281528, compound

Product 1

HCID 44189333HCID 44189333, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A dichloromethane (13 mL) solution of 2-(3,4-dichlorophenyl)-3-hydroxy-4-methylcarbonyl-5-methyl-2,5-dihydrothiophene (806 mg, 2.66 mmol) was cooled to −72° C., and to this solution, a dichloromethane (2.7 mL) solution of sulfuryl chloride (0.11 mL, 0.5 equivalent amount) was dropwise added over a period of 3 minutes. After the temperature of the solution was raised to room temperature, the solution was mixed with water (16 mL) and a saturated sodium chloride aqueous solution (16 mL), and extracted with dichloromethane. The dichloromethane solution was dried over a drying agent and purified by silica gel column chromatography (eluent: hexane/ethyl acetate=85/15 and then 4/1 (v/v)) to give the desired product as a yellow solid (0.25 g, yield: 31%).

Workup

  1. extractiona saturated sodium chloride aqueous solution (16 mL), and extracted with dichloromethane
  2. dry with materialThe dichloromethane solution was dried over a drying agent
  3. custompurified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-2fb58bec23514568a4e816b2ab31bced
Source dataset
uspto-grants-2013_03
Patent number
US08399685B2

Reaction notes

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