Triethylamine → 2-Furanethanol, tetrahydro-, 2-methanesulfonate

HRID 1010936Notes

Reaction equation

HRID 1010936 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][CH2:7][OH:8].C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>ClCCl>[CH3:16][S:17]([O:8][CH2:7][CH2:6][CH:2]1[CH2:3][CH2:4][CH2:5][O:1]1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 119895722-(Oxolan-2-yl)ethan-1-ol

Product 1

HCID 576996872-Furanethanol, tetrahydro-, 2-methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cooled stirring solution of 2-(tetrahydrofuran-2-yl)ethanol (1.9 g) and triethylamine (4.4 ml) in dry dichloromethane (30 ml) was added dropwise over 5 min methanesulphonyl chloride (1.59 ml). The mixture was allowed to warm slowly to ambient temperature over 16 h then washed with saturated sodium hydrogen carbonate. The aqueous layer was further extracted with dichloromethane and the combined extracts washed with brine, dried by passing through a phase separation cartridge and stripped to give the title compound as a light brown oil, yield 3.1 g.

Workup

  1. washthen washed with saturated sodium hydrogen carbonate
  2. extractionThe aqueous layer was further extracted with dichloromethane
  3. washthe combined extracts washed with brine
  4. customdried
  5. customby passing through a phase separation cartridge

Sources & evidence

ORD record
ord-91cbba8f2cc948cd933467443e275cda
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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