Triethylamine → Oxolan-3-yl methanesulfonate

HRID 2090434Notes

Reaction equation

HRID 2090434 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][O:4][CH2:3]1.[CH3:7][S:8](Cl)(=[O:10])=[O:9].C(N(CC)CC)C>C(Cl)Cl>[CH3:7][S:8]([O:1][CH:2]1[CH2:6][CH2:5][O:4][CH2:3]1)(=[O:10])=[O:9]

Participants

5

Reactant 3

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

Product 1

HCID 15278452Oxolan-3-yl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-hydroxytetrahydrofuran (100 mg, 1 mmol, Aldrich, Cat. No. H59109), methanesulfonyl chloride (100.0 uL, 1.4 mmol), triethylamine (350 uL, 2.5 mmol) in methylene chloride (2 mL) was stirred at r.t. for 2 hours. It was diluted with methylene chloride, washed with water, brine; dried over Na2SO4. After filtration the filtrate was concentrated to yield 180 mg of the product which was directly used in the next step reaction without further purification.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration the filtrate
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-9a777cd5997e43a883e3de113c0e9d89
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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