Water → 1-(2-Chloromethylcyclohex-1-enyl)-3-nitrobenzene

HRID 1842184Notes

Reaction equation

HRID 1842184 reaction equation
C(N(CC)C(C)C)(C)C.[N+:10]([C:13]1[CH:14]=[C:15]([C:19]2[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=2[CH2:25]O)[CH:16]=[CH:17][CH:18]=1)([O-:12])=[O:11].CS([Cl:31])(=O)=O.O>ClCCl>[Cl:31][CH2:25][C:20]1[CH2:21][CH2:22][CH2:23][CH2:24][C:19]=1[C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 57827168[2-(3-Nitrophenyl)cyclohex-1-enyl]methanol

Product 1

HCID 578277541-(2-Chloromethylcyclohex-1-enyl)-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-Diisopropylethylamine (3.64 mL) was added to a solution of [2-(3-nitrophenyl)cyclohex-1-enyl]methanol obtained in Preparation Example 4-(2) (1.67 g) in dichloromethane (109 mL) in an ice bath. Then, methanesulfonyl chloride (668 μL) was added dropwise. The reaction mixture was warmed to room temperature and stirred overnight. Water was added to the reaction mixture, followed by extraction with ethyl acetate. 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 (1.56 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  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-c50dbc9835a24d508d8944c84987ac35
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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