Triethylamine → Oxan-4-ylmethyl methanesulfonate

HRID 1010993Notes

Reaction equation

HRID 1010993 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][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:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2773573(Oxan-4-yl)methanol

Product 1

HCID 15166436Oxan-4-ylmethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tetrahydro-2H-pyran-4-ylmethanol (6.2 g) in dry dichloromethane (226.3 ml) at 0° C. and under nitrogen, was added triethylamine (18.1 ml), followed by mesyl chloride (5.4 ml). The reaction was allowed to warm to room temperature and left at this temperature overnight. The reaction mixture was washed with saturated aqueous sodium bicarbonate (200 ml). The organic layer was separated, passed through a hydrophobic frit to dry and concentrated in vacuo to yield a light brown lumpy solid (10.17 g).

Workup

  1. washThe reaction mixture was washed with saturated aqueous sodium bicarbonate (200 ml)
  2. customThe organic layer was separated
  3. customto dry
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c79bcc0a48f4c788f711db359048136
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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