Triethylamine → 2-(Tetrahydro-2H-pyran-4-yl)ethyl methanesulfonate

HRID 1010944

Reaction equation

HRID 1010944 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][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:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 177509442-(Oxan-4-yl)ethan-1-ol

Product 1

HCID 222730832-(Tetrahydro-2H-pyran-4-yl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-(tetrahydro-2H-pyran-4-yl)ethanol (3,3 g) in dry dichloromethane (100 ml) at 0° C. and under nitrogen was added triethylamine (4.6 ml), followed by methanesulphonyl chloride (2.6 ml) dropwise over 5 minutes. The reaction was stirred until the ice in the bath melted and left overnight at room temperature. The reaction was washed with saturated aqueous sodium bicarbonate (40 ml). The organic layer was dried by passing through a hydrophobic frit and concentrated in vacuo to yield the title compound as a yellow oil (5.4 g).

Workup

  1. washThe reaction was washed with saturated aqueous sodium bicarbonate (40 ml)
  2. customThe organic layer was dried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9d4b9e3c68084152b087ac5b379cc57c
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Linked notes

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