Triethylamine → (Tetrahydrofuran-3-yl)methyl methanesulfonate

HRID 1011050Notes

Reaction equation

HRID 1011050 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][OH:7])[CH2:2]1.C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>ClCCl>[CH3:15][S:16]([O:7][CH2:6][CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 139980Tetrahydro-3-furanmethanol

Product 1

HCID 22273010(Tetrahydrofuran-3-yl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To tetrahydro-3-furanylmethanol, Isomer 1 (1.3 g) in dry dichloromethane (40 ml) at 0° C. and under nitrogen, was added triethylamine (4.09 ml) followed by methanesulfonyl chloride (1.29 ml). The reaction was stirred at room temperature overnight. The orange solution was diluted with dichloromethane (80 ml) and washed with saturated aqueous sodium bicarbonate (40 ml). The organic layer was separated, dried through a hydrophobic frit and concentrated in vacuo to yield the title compound as a yellow oil (2.2 g).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (40 ml)
  2. customThe organic layer was separated
  3. customdried through a hydrophobic frit
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d04099a088cd4ad395e0691e522fc849
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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