Water → 2-(Tetrahydro-3-furanyl)ethyl methanesulfonate

HRID 1822804Notes

Reaction equation

HRID 1822804 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[O:13]1[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][OH:20])[CH2:14]1.O>ClCCl>[O:13]1[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][O:20][S:9]([CH3:8])(=[O:11])=[O:10])[CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 111262252-(Oxolan-3-yl)ethan-1-ol

Product 1

HCID 576998222-(Tetrahydro-3-furanyl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (2.1 mL, 15 mM) and methanesulfonyl chloride (0.85 mL, 11 mM) were added drop wise to a cold (−5 to −10° C.) solution of 2-(tetrahydro-furan-3-yl)-ethanol (1.14 g, 10 mM) in dichloromethane (15 mL). The reaction was stirred for 20 min at this temp then water (10 mL) was added and the reaction was stirred an additional 10 min then the phases were separated and the aqueous phase was extracted with dichloromethane (3×20 mL). The combined organics were washed with 50% aqueous HCl, sat. NaHCO3, dried (MgSO4), filtered and concentrated to give a quantitative yield of methanesulfonic acid 2-(tetrahydrofuran-3-yl)-ethyl ester.

Workup

  1. stirringthe reaction was stirred an additional 10 min
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with dichloromethane (3×20 mL)
  4. washThe combined organics were washed with 50% aqueous HCl, sat. NaHCO3
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0cf4456c3d2a47fda913514d5819e869
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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