Triethylamine → Methanesulfonic acid 3-chloro-1-phenyl-propyl ester

HRID 250204Notes

Reaction equation

HRID 250204 reaction equation
[Cl:1][CH2:2][CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[Cl:1][CH2:2][CH2:3][CH:4]([O:5][S:20]([CH3:19])(=[O:22])=[O:21])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5720643-Chloro-1-phenylpropanol

Product 1

HCID 57985877Methanesulfonic acid 3-chloro-1-phenyl-propyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R) 3-chloro-1-phenyl-propan-1-ol (Aldrich) (0.250 g) in 40 ml dichloromethane was added triethylamine (0.272 g) at 0° C. followed by the dropwise addition of methanesulfonyl chloride (0.185 g). The reaction mixture was stirred at this temperature for 2 hours and then quenched by the addition of sodium bicarbonate solution. The phases were separated and the organic phase was evaporated to dryness to afford methanesulfonic acid 3-chloro-1-phenyl-propyl ester as an oil which was used directly in the next step.

Workup

  1. customquenched by the addition of sodium bicarbonate solution
  2. customThe phases were separated
  3. customthe organic phase was evaporated to dryness

Sources & evidence

ORD record
ord-72042448726a4ed8b875b18bf2166633
Source dataset
uspto-grants-2011_01
Patent number
US07863305B2

Reaction notes

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