4-Toluenesulfonyl chloride → Tetrahydrofuran-3-YL 4-methylbenzenesulfonate, (3R)-

HRID 2194559Notes

Reaction equation

HRID 2194559 reaction equation
[O:1]1[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]1.[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>C(Cl)Cl>[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:6][C@@H:3]2[CH2:4][CH2:5][O:1][CH2:2]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 641512(-)-3-Hydroxytetrahydrofuran

Product 1

HCID 11149197Tetrahydrofuran-3-YL 4-methylbenzenesulfonate, (3R)-Yield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (R)-tetrahydrofuran-3-ol (1 g, 11.4 mmole) and TEA (2.3 g, 22.8 mmole) in DCM (20 mL) at 0° C. was added dropwise 4-methylbenzene-1-sulfonyl chloride (2.2 g, 11.4 mmole). The resulting mixture was stirred at room temperature for 8 h. The mixture was washed with water, dried over MgSO4, filtered, and concentrated. The crude product was purified by ISCO (silica gel, eluting with 15% ethyl acetate in hexane) to give the title compound (2.3 g). MS (ESI) m/z: Found: 243.3 (M++1). Calc. 242.3 (M+).

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by ISCO (silica gel, eluting with 15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b5b571d0b54e4110949d6027a41e8b51
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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