Water → (S)-tetrahydrofuran-3-yl methanesulfonate

HRID 874390Notes

Reaction equation

HRID 874390 reaction equation
[O:1]1[CH2:5][CH2:4][C@H:3]([OH:6])[CH2:2]1.C(N(CC)CC)C.[CH3:14][S:15](Cl)(=[O:17])=[O:16].O>C(Cl)Cl>[CH3:14][S:15]([O:6][C@H:3]1[CH2:4][CH2:5][O:1][CH2:2]1)(=[O:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2733227(S)-(+)-3-Hydroxytetrahydrofuran

Product 1

HCID 57561588(S)-tetrahydrofuran-3-yl methanesulfonateYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (S)-tetrahydrofuran-3-ol (1.0 g, 11 mmol) and triethylamine (9.4 mL, 86 mmol) in CH2Cl2 (20 mL) was cooled in an ice-water bath. To this, methanesulfonyl chloride (3.0 mL, 39 mmol) diluted in CH2Cl2 (10 mL) was added dropwise. The reaction was left stirring for 12 hours at room temperature. Water was added, and organic phases extracted in CH2Cl2 (3×50 mL), which were subsequently dried onto silica and purified by silica gel chromatography (50% EtOAc:Hexanes to 100% EtOAc gradient) to afford (S)-tetrahydrofuran-3-yl methanesulfonate (1.52 g, brown oil, 83% yield).

Workup

  1. additionwas added dropwise
  2. waitThe reaction was left
  3. extractionorganic phases extracted in CH2Cl2 (3×50 mL)
  4. customwhich were subsequently dried onto silica
  5. custompurified by silica gel chromatography (50% EtOAc:Hexanes to 100% EtOAc gradient)

Sources & evidence

ORD record
ord-0f31010e524b41c087dbe5f4c7a1b242
Source dataset
uspto-grants-2015_03
Patent number
US08980899B2

Reaction notes

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