Water → HCID 57827368, compound

HRID 1693143Notes

Reaction equation

HRID 1693143 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[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=1[CH2:23]O.CS([Cl:29])(=O)=O.O>ClCCl>[Cl:29][CH2:23][C:18]1[CH2:19][CH2:20][CH2:21][CH2:22][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 57827171HCID 57827171, compound

Product 1

HCID 57827368HCID 57827368, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-Diisopropylethylamine (14.7 mL) was added to a solution of [2-(2-fluorophenyl)cyclohex-1-enyl]methanol obtained in Preparation Example 1-(3) (8.88 g) in dichloromethane (300 mL). Methanesulfonyl chloride (4.00 mL) was added dropwise to the reaction solution in an ice bath. The reaction solution was gradually warmed to room temperature and stirred overnight. Water was added to the reaction solution, 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 resulting crude product was purified by silica gel column chromatography to obtain the title compound (5.88 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 resulting crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a26ee39965a54b07b24be8e854d9eb4a
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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