Water → Toluene-4-sulfonic acid tetrahydro-furan-3-ylmethyl ester

HRID 78454

Reaction equation

HRID 78454 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][OH:7])[CH2:2]1.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.O>C(Cl)Cl.N1C=CC=CC=1>[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][O:7][S:14]([C:11]2[CH:12]=[CH:13][C:8]([CH3:18])=[CH:9][CH:10]=2)(=[O:16])=[O:15])[CH2:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 139980Tetrahydro-3-furanmethanol

Product 1

HCID 15335290Toluene-4-sulfonic acid tetrahydro-furan-3-ylmethyl esterYield 98.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tetrahydro-3-furanmethanol (Aldrich, 1.0 mL, 10.4 mmol) in 5 mL CH2Cl2 and 5 mL pyridine was added para-toluenesulfonyl chloride (3.0 g, 15.6 mmol) portion-wise over 15 minutes. This mixture stirred at ambient temperature for 3 hours then 5 mL H2O was added. The layers were separated and the aqueous layer was extracted 2×5 mL CH2Cl2. The combined organics were dried over Na2SO4, filtered, concentrated under reduced pressure and dried under vacuum (˜1 mm Hg) to afford the title compound (2.62 g, 10.2 mmol, 98% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.49-1.63 (m, 1H) 1.94-2.08 (m, 1H) 2.46 (s, 3H) 2.52-2.68 (m, 1H) 3.49 (dd, J=9.16, 5.09 Hz, 1H) 3.64-3.84 (m, 3H) 3.88-4.03 (m, 2H) 7.36 (d, J=8.14 Hz, 2H) 7.76-7.82 (m, 2H); MS (DCI/NH3) m/z 257 (M+H)+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted 2×5 mL CH2Cl2
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customdried under vacuum (˜1 mm Hg)

Sources & evidence

ORD record
ord-a63ad7606a09434aa78d69d6c6673cb6
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Linked notes

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