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

HRID 433327Notes

Reaction equation

HRID 433327 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 concentrated 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. concentrationThe reaction solution is concentrated 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-f8012c38a02747b19712a0db29e4da11
Source dataset
uspto-grants-2003_12
Patent number
US06667345B2

Reaction notes

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