Triethylamine → 2-(Tetrahydro-2H-pyran-3-yl)ethyl methanesulfonate

HRID 1010941Notes

Reaction equation

HRID 1010941 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][CH2:8][OH:9])[CH2:2]1.C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl>[CH3:17][S:18]([O:9][CH2:8][CH2:7][CH:3]1[CH2:4][CH2:5][CH2:6][O:1][CH2:2]1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 55264768Tetrahydro-2H-pyran-3-ethanol

Product 1

HCID 576996182-(Tetrahydro-2H-pyran-3-yl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(tetrahydro-2H-pyran-3-yl)ethanol (1.54 gm) and triethylamine (3.3 ml) in dichloromethane (25 ml) was cooled (ice bath) and methanesulphonyl chloride (1.19 ml) added dropwise with stirring over 5 min. The reaction slowly warmed to ambient temperature as the ice bath melted. After 16 h the mixture was washed with saturated aq. sodium hydrogen carbonate, the aqueous layer extracted twice with dichloromethane and the combined extracts washed with dilute brine, dried by passing through a hydrophobic frit and evaporated to give the title compound as a brown oil, yield 2.38 g.

Workup

  1. additionadded dropwise
  2. customThe reaction
  3. washAfter 16 h the mixture was washed with saturated aq. sodium hydrogen carbonate
  4. extractionthe aqueous layer extracted twice with dichloromethane
  5. washthe combined extracts washed with dilute brine
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-7e0e59a12b9340a694be76a51c5abadb
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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