Triethylamine → Tetrahydro-2H-pyran-3-ylmethyl methanesulfonate

HRID 1010992Notes

Reaction equation

HRID 1010992 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][OH:8])[CH2:2]1.C(N(CC)CC)C.[S:16](Cl)([CH3:19])(=[O:18])=[O:17]>ClCCl>[CH3:19][S:16]([O:8][CH2:7][CH:3]1[CH2:4][CH2:5][CH2:6][O:1][CH2:2]1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 85769Tetrahydro-2H-pyran-3-methanol

Product 1

HCID 22402475Tetrahydro-2H-pyran-3-ylmethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tetrahydro-2H-pyran-3-ylmethanol (4.92 g) in dry dichloromethane (140 ml) at 0° C. and under nitrogen, was added anhydrous triethylamine (13.6 ml) in one go, followed by mesyl chloride (4.3 ml) dropwise over 5 minutes. The reaction was allowed to warm to room temperature and stirred at this temperature overnight. The reaction was quenched with saturated aqueous sodium bicarbonate (50 ml). The organic layer was separated, passed through a hydrophobic frit to dry and concentrated in vacuo to yield a red oil (8.8 g).

Workup

  1. customThe reaction was quenched with saturated aqueous sodium bicarbonate (50 ml)
  2. customThe organic layer was separated
  3. customto dry
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-da1ea2a94585412492498f6165dd4248
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

Loading…