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

HRID 237453

Reaction equation

HRID 237453 reaction equation
[O:1]1[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]1.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1>ClCCl.N1C=CC=CC=1>[O:1]1[CH2:5][CH2:4][C@@H:3]([O:6][S:13]([C:10]2[CH:11]=[CH:12][C:7]([CH3:17])=[CH:8][CH:9]=2)(=[O:15])=[O:14])[CH2:2]1

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (R)-tetrahydrofuran-3-ol (25.4 g) in dichloromethane (250 mL) and pyridine (60 mL) is added at 0° C. N,N-dimethylaminopyridine (DMAP; 1 g) and p-toluene-sulfonylchloride (73 g) in portions. The mixture is stirred for 12 hours at room temperature, diluted with dichloromethane and washed with 1 M aqueous HCl solution and brine. After drying (MgSO4) the solvent is evaporated and the residue is chromatographed on silica gel (dichloromethane/methanol 100:0→95:5) to give the title compound. Yield: 59.5 g; Mass spectrum (ESI+): m/z=243 [M+H]+.

Workup

  1. washwashed with 1 M aqueous HCl solution and brine
  2. dry with materialAfter drying (MgSO4) the solvent
  3. customis evaporated
  4. customthe residue is chromatographed on silica gel (dichloromethane/methanol 100:0→95:5)

Sources & evidence

ORD record
ord-c0a99b9bb1964f56b30ad28a2897bf38
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Linked notes

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