Water → HCID 57827260, compound

HRID 1693148Notes

Reaction equation

HRID 1693148 reaction equation
C(N(CC)C(C)C)(C)C.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH2:21][CH2:20][CH2:19][C:18]=1[CH2:22]O.CS([Cl:28])(=O)=O.O>ClCCl>[Cl:28][CH2:22][C:18]1[CH2:19][CH2:20][CH2:21][C:17]=1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[F:10]

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 57827596HCID 57827596, compound

Product 1

HCID 57827260HCID 57827260, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-Diisopropylethylamine (17.2 mL) was added to a solution of [2-(2-fluorophenyl)cyclopent-1-enyl]methanol obtained in Preparation Example 3-(3) (6.50 g) in dichloromethane (300 mL) in an ice bath. Methanesulfonyl chloride (2.88 mL) was added to the reaction solution at the same temperature. Then, the reaction solution was warmed to room temperature and stirred overnight. Water was added to the reaction mixture, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (7.23 g).

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe drying agent was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0a2f4e904ad748949fab983b0e958ba6
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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