4-Toluenesulfonyl chloride → (S)-tetrahydrofuran-3-yl 4-methylbenzenesulfonate

HRID 2194591Notes

Reaction equation

HRID 2194591 reaction equation
[O:1]1[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]1.CCN(CC)CC.[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>C(Cl)Cl>[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O:6][C@H:3]2[CH2:4][CH2:5][O:1][CH2:2]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 641512(-)-3-Hydroxytetrahydrofuran

Product 1

HCID 13837326(S)-tetrahydrofuran-3-yl 4-methylbenzenesulfonateYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tetrahydrofuran-3-ol (3 g, 34.1 mmole) and Et3N (6.9 g, 68.2 mmole) in DCM (40 mL) at 0° C. was added 4-methylbenzene-1-sulfonyl chloride (7.2 g, 37.5 mmole. The mixture was stirred at room temperature for 8 h. The mixture was washed with water, dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 15% ethyl acetate in hexane) to give the title compound (6.8 g, 83% yield). MS (ESI) m/z: Calc. 242.1 (M+). Found: 243.1 (M++1).

Workup

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

Sources & evidence

ORD record
ord-a407739f37f84ca9adcc4d18246f1eb2
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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