Triethylamine → Oxolan-3-yl methanesulfonate

HRID 510488Notes

Reaction equation

HRID 510488 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.C(N(CC)CC)C.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C(Cl)Cl>[CH3:14][S:15]([O:6][CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 99603-Furanol, tetrahydro-HCID 31297Methanesulfonyl chloride

Product 1

HCID 15278452Oxolan-3-yl methanesulfonateYield 175.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-tetrahydrofuranol (1 g, 6.5 mmol) in DCM (10 mL) was added triethylamine (1.9 mL, 13.6 mmol). The reaction mixture was stirred for 15 minutes at room temperature. To the reaction mixture was added methanesulfonyl chloride (1.08 mL, 13.6 mmol) at 0° C. The reaction mixture was stirred for a further 18 h. The reaction mixture was then quenched by addition of water, and diluted with EtOAc. The organic layer was washed with water and brine, dried over sodium sulphate and concentrated to yield the title compound (1.9 g, 88%). δH (CDCl3) 5.32 (m, 1H), 4.10-3.80 (m, 4H), 3.70 (s, 3H), 2.30-2.20 (m, 2H).

Workup

  1. stirringThe reaction mixture was stirred for a further 18 h
  2. customThe reaction mixture was then quenched by addition of water
  3. additiondiluted with EtOAc
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-15ccac40367f449080f93b7b11605ca4
Source dataset
uspto-grants-2015_08
Patent number
US09096614B2

Reaction notes

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