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

HRID 1054455Notes

Reaction equation

HRID 1054455 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]>C(Cl)Cl>[CH3:17][S:14]([O:6][C@H:3]1[CH2:4][CH2:5][O:1][CH2:2]1)(=[O:16])=[O:15]

Participants

5

Reactant 3

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

Product 1

HCID 57561588(S)-tetrahydrofuran-3-yl methanesulfonateYield 93.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tetrahydrofuran-3-ol (25.0 g, 283 mmol) in 150 ml of DCM was cooled to 0° C., to this was added triethylamine (59 ml, 425 mmol) and mesylchloride (26.0 ml, 340 mmol), stirred the reaction mixture for 4 h at room temperature. TLC indicated reaction completion, it was diluted with DCM (100 ml), washed with water and brine solution, dried over anhydrous sodium sulfate, organic layer was evaporated to yields (44.0 g) of title product which was used as such for the next step.

Workup

  1. customreaction completion, it
  2. washwashed with water and brine solution
  3. dry with materialdried over anhydrous sodium sulfate, organic layer
  4. customwas evaporated

Sources & evidence

ORD record
ord-8b7b7d26f0474ae9855adc790dff7a76
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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