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3-(Methylthio)-1-propanol → 3-(Methylsulfanyl)propyl methanesulfonate

HRID 561873
Notes
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Reaction equation

HRID 561873 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH2:5][OH:6].CCN(C(C)C)C(C)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>ClCCl>[CH3:16][S:17]([O:6][CH2:5][CH2:4][CH2:3][S:2][CH3:1])(=[O:19])=[O:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 104483-(Methylthio)-1-propanolHCID 31297Methanesulfonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 229318563-(Methylsulfanyl)propyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Procedure

To a solution of 3-(methylthio)propan-1-ol in dichloromethane (0.2 M) was added sequentially at −78° C. Hunig's base (1.3 eq.) and methanesulfonyl chloride (1.3 eq.). The resulting reaction mixture was stirred at −78° C. for 1 h and then warmed slowly to RT. The reaction was quenched with sat. aq. NH4Cl and then extracted with ether. The combined organic extracts were washed with water and brine, dried over MgSO4, and filtered. Concentrated of the filtrate in vacuo afforded the title compound as a yellow oil.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewarmed slowly to RT
  3. customThe reaction was quenched with sat. aq. NH4Cl
  4. extractionextracted with ether
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationConcentrated of the filtrate in vacuo

Sources & evidence

ORD record
ord-deb24d9f41844cfbaf0712a398b6063c
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063105B2

Reaction notes

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