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

HRID 844582Notes

Reaction equation

HRID 844582 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:8]=[C:9]([C@@H: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]([C@@H: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 18392749(2S)-2-(3,4-dichlorophenyl)pent-4-en-1-ol

Product 1

HCID 540787524(S)-(3,4-dichlorophenyl)-5-(methanesulphonyloxy)pent-1-eneYield 102.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulphonyl chloride (3.55 g) was added dropwise to an ice-cooled solution of 4(S)-(3,4-dichlorophenyl)-5-hydroxypent-1-ene (6.0 g) (see Preparation 91) and triethylamine (3.48 g) in dichloromethane (100 ml) and the mixture stirred at room temperature for 1 hour. The solvent was then removed under reduced pressure and the residue partitioned between diethyl ether and water. The two phases were separated and the aqueous layer further extracted with diethyl ether. The organic phases were then combined and washed sequentially with water, dilute aqueous citric acid solution, brine, saturated aqueous sodium hydrogen carbonate solution and brine before drying over anhydrous sodium sulphate. Removal of the solvent under reduced pressure gave 4(S)-(3,4-dichlorophenyl)-5-(methanesulphonyloxy)pent-1-ene (8.25 g) as an oil.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe residue partitioned between diethyl ether and water
  3. customThe two phases were separated
  4. extractionthe aqueous layer further extracted with diethyl ether
  5. washwashed sequentially with water, dilute aqueous citric acid solution, brine, saturated aqueous sodium hydrogen carbonate solution and brine
  6. dry with materialbefore drying over anhydrous sodium sulphate
  7. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-9104799f69544236844f30f908c735de
Source dataset
uspto-grants-2002_04
Patent number
US06380396B1

Reaction notes

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