4-Toluenesulfonyl chloride → HCID 59267964, compound

HRID 384470

Reaction equation

HRID 384470 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>N1C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][O:9][S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=2)(=[O:18])=[O:17])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 177509442-(Oxan-4-yl)ethan-1-ol

Product 1

HCID 59267964HCID 59267964, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To an ice-cold solution of 2-(tetrahydro-2H-pyran-4-yl)ethanol (1.00 g) in pyridine (6.5 mL) was added p-toluenesulfonyl chloride (1.5 g), followed by stirring at the same temperature for 30 minutes, and at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and then diluted aqueous hydrochloric acid (20 mL) was added to the residue, followed by twice extractions with ethyl acetate (20 mL). The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=80/20-50/50) to obtain p-toluenesulfonic acid 2-(tetrahydro-2H-pyran-4-yl)ethyl ester (450 mg).

Workup

  1. waitat room temperature for 18 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiondiluted aqueous hydrochloric acid (20 mL) was added to the residue
  4. extractionfollowed by twice extractions with ethyl acetate (20 mL)
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=80/20-50/50)

Sources & evidence

ORD record
ord-9eef5ea75a144a9e8b5f1833e420e532
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Linked notes

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