Triethylamine → 4-(3,4-Dichlorophenyl)-5-(methanesulphonyloxy)pent-1-ene

HRID 1533043Notes

Reaction equation

HRID 1533043 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:8]=[C:9]([CH:14]([CH2:18][OH:19])[CH2:15][CH:16]=[CH2:17])[CH:10]=[CH:11][C:12]=1[Cl:13].C(N(CC)CC)C>ClCCl>[Cl:6][C:7]1[CH:8]=[C:9]([CH:14]([CH2:18][O:19][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:15][CH:16]=[CH2:17])[CH:10]=[CH:11][C:12]=1[Cl:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 225936544-(3,4-Dichlorophenyl)-5-hydroxypent-1-ene

Product 1

HCID 226137984-(3,4-Dichlorophenyl)-5-(methanesulphonyloxy)pent-1-eneYield 93.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulphonyl chloride (2.3 g) in dichloromethane (10 ml) was added to an ice-cooled solution of 4-(3,4-dichlorophenyl)-5-hydroxypent-1-ene (4.3 g) (see Preparation 22) and triethylamine (2.5 g) in dichloromethane (50 ml) over 10 minutes. The mixture was stirred for a further 30 minutes before being washed sequentially with water (3×25 ml) and brine (25 ml), then dried over anhydrous sodium sulphate. Removal of the solvent under reduced pressure gave 4-(3,4-dichlorophenyl)-5-(methanesulphonyloxy)pent-1-ene (5.4 g) as an oil.

Workup

  1. washbefore being washed sequentially with water (3×25 ml) and brine (25 ml)
  2. dry with materialdried over anhydrous sodium sulphate
  3. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-42f141ebf11740f9bcbf3128ec1d8dd4
Source dataset
uspto-grants-2001_03
Patent number
US06207678B1

Reaction notes

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