Triethylamine → (S)-1-(3,5-Dichloropyridin-4-yl)ethyl methanesulfonate

HRID 2387414Notes

Reaction equation

HRID 2387414 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:11])[C:7]=1[C@@H:8]([OH:10])[CH3:9].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[CH3:19][S:20]([O:10][C@H:8]([C:7]1[C:2]([Cl:1])=[CH:3][N:4]=[CH:5][C:6]=1[Cl:11])[CH3:9])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66831621(S)-1-(3,5-Dichloropyridin-4-yl)ethanol

Product 1

HCID 86647459(S)-1-(3,5-Dichloropyridin-4-yl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve (S)-1-(3,5-dichloropyridin-4-yl)ethanol (5.02 g, 26.14 mmol) in dichloromethane (DCM, 100 mL) and cool the flask in an ice bath. Add triethylamine (TEA, 3.5 mL, 25.11 mmol) followed by the dropwise addition of methanesulfonyl chloride (2.2 mL, 28.42 mmol). Remove the ice bath and allow the reaction to warm to RT. After 4 hours, quench the reaction with water (100 mL) and separate layers. Extract the aqueous layer with DCM (50 mL) followed by 20% isopropyl alcohol (IPA)/chloroform (50 mL). Combine the organic extracts, dry over anhydrous sodium sulfate, filter and concentrate in vacuo. Yield: 7.15 g, (100%). MS (ES) m/z 270 [M+1]+.

Workup

  1. temperaturecool the flask in an ice bath
  2. customRemove the ice bath
  3. customthe reaction
  4. customquench
  5. customthe reaction with water (100 mL)
  6. customseparate layers
  7. extractionExtract the aqueous layer with DCM (50 mL)
  8. dry with materialCombine the organic extracts, dry over anhydrous sodium sulfate
  9. filtrationfilter
  10. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-15f610aa2a3e45548112c5ad14e2000b
Source dataset
uspto-grants-2012_09
Patent number
US08268869B2

Reaction notes

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