Water → Oxolan-3-yl methanesulfonate

HRID 1357014Notes

Reaction equation

HRID 1357014 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.C(N(CC)CC)C.[S:14](Cl)([CH3:17])(=[O:16])=[O:15].O>C(Cl)Cl>[O:1]1[CH2:5][CH2:4][CH:3]([O:6][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 99603-Furanol, tetrahydro-HCID 31297Methanesulfonyl chloride

Product 1

HCID 15278452Oxolan-3-yl methanesulfonateYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of tetrahydrofuran-3-ol (4.6 g, 52.2 moles) in methylene chloride (70 ml) at 0° C. was added with triethylamine (8.36 ml, 60 moles) and mesyl chloride (4.44 ml, 57.4 moles) in methylene chloride (85 ml). The temperature was left to rise to room value and after 1 hour the mixture was poured into water and in methylene chloride. The organic phases were anhydrified and dried to give 8.12 g of the title product (yield: 93%).

Workup

  1. waitThe temperature was left
  2. customdried

Sources & evidence

ORD record
ord-c12c015d6978485db56efb14b74edc5a
Source dataset
uspto-grants-2003_07
Patent number
US06589951B1

Reaction notes

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