Pyridine → 1-Acetoxy-5-chloro-2-methylsulfonylindane

HRID 2084731Notes

Reaction equation

HRID 2084731 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([OH:11])[CH:6]([S:12]([CH3:15])(=[O:14])=[O:13])[CH2:5]2.N1C=CC=CC=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>ClCCl>[C:22]([O:11][CH:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH2:5][CH:6]1[S:12]([CH3:15])(=[O:14])=[O:13])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 98347545-Chloro-2-methylsulfonylindan-1-ol

Product 1

HCID 99438231-Acetoxy-5-chloro-2-methylsulfonylindane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.247 g (1 mmol) of 5-chloro-2-methylsulfonylindan-1-ol is dissolved in 5 ml of dichloromethane. 1 ml of pyridine and 1 ml of acetic anhydride are added to the solution, and the reaction mixture is then stirred at room temperature for 2 days. The reaction solution is evaporated completely and the residue is taken up in dichloromethane and extracted with dilute citric acid. The organic phase is separated off, concentrated and purified chromatographically (silica gel; dichloromethane/methanol 20/1). This gives 1-acetoxy-5-chloro-2-methylsulfonylindane of melting point 136° C.

Workup

  1. customThe reaction solution is evaporated completely
  2. extractionextracted with dilute citric acid
  3. customThe organic phase is separated off
  4. concentrationconcentrated
  5. custompurified chromatographically (silica gel; dichloromethane/methanol 20/1)

Sources & evidence

ORD record
ord-c44c60862176409b930be4ea56700993
Source dataset
uspto-grants-2004_04
Patent number
US06717008B2

Reaction notes

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