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

HRID 911456Notes

Reaction equation

HRID 911456 reaction equation
[O:1]1[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]1.C(N(CC)CC)C.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl.[Ag]=O>[O:1]1[CH2:5][CH2:4][C@@H:3]([O:6][S:20]([C:17]2[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=2)(=[O:22])=[O:21])[CH2:2]1

Participants

7

Reactant 3

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

Product 1

HCID 11149197Tetrahydrofuran-3-YL 4-methylbenzenesulfonate, (3R)-Yield 85.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 92152Silver(II) oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To (R)-tetrahydro-furan-3-ol (2.0 g, 22.7 mmol), triethylamine (3.8 mL, 27.3 mmol), DMAP (277 mg, 2.26 mmol), and silver oxide (5.26 g, 22.7 mmol) in dry DCM (30 mL) at 0° C. under nitrogen, add portion wise with stirring p-toluenesulfonyl chloride (4.76 g, 25.0 mmol). Warm to ambient temperature overnight, filter from silver salts, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (7:1) to give the title compound as a clear liquid (4.7 g, 85%).

Workup

  1. filtrationfilter from silver salts
  2. concentrationconcentrate in vacuo
  3. customPurify by chromatography on silica gel eluting with hexane/EtOAc (7:1)

Sources & evidence

ORD record
ord-3e79d1a5cb24485baaae885eca341f15
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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