Triethylamine → 2-(2-Chlorophenyl)ethyl methanesulfonate

HRID 440934Notes

Reaction equation

HRID 440934 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10].C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>O1CCCC1>[CH3:18][S:19]([O:10][CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 88266o-Chlorophenethylic alcohol

Product 1

HCID 218880872-(2-Chlorophenyl)ethyl methanesulfonateYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.26 mL (40 mMol) 2-(2-chlorophenyl)ethanol and 8.36 mL (60 mMol) triethylamine in 100 mL tetrahydrofuran were added dropwise 3.25 mL (42 mMol) methanesulfonyl chloride with cooling. The reaction mixture was stirred 4 hours at ambient and was then concentrated under reduced pressure. The residue was partitioned between dichloromethane and water. The organic phase was separated and washed sequentially with water and saturated aqueous sodium chloride. The remaining organics were dried over sodium sulfate and concentrated under reduced pressure to give 9.22 gm (98.3%) of the title compound as a yellow oil. The product was used without further purification.

Workup

  1. temperaturewith cooling
  2. concentrationwas then concentrated under reduced pressure
  3. customThe residue was partitioned between dichloromethane and water
  4. customThe organic phase was separated
  5. washwashed sequentially with water and saturated aqueous sodium chloride
  6. dry with materialThe remaining organics were dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-71731d44936e4ba7b5b4d009fd53129c
Source dataset
uspto-grants-1996_05
Patent number
US05521197

Reaction notes

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