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

HRID 1533063Notes

Reaction equation

HRID 1533063 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 firrter extracted with diethyl ether. The organic pahses 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 firrter 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-a37e1504bb344d169a898a3a53f099e2
Source dataset
uspto-grants-2001_03
Patent number
US06207678B1

Reaction notes

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