Dichloromethane → 3-(Cyclopropyloxy)propyl p-toluenesulfonate

HRID 69128Notes

Reaction equation

HRID 69128 reaction equation
[CH:1]1([O:4][CH2:5][CH2:6][CH2:7][OH:8])[CH2:3][CH2:2]1.ClCCl.C(N(CC)CC)C.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(Cl)(Cl)Cl>[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25]([O:8][CH2:7][CH2:6][CH2:5][O:4][CH:1]2[CH2:3][CH2:2]2)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 666961453-Cyclopropoxypropan-1-ol

Product 1

HCID 866943303-(Cyclopropyloxy)propyl p-toluenesulfonateYield 44.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 500 mg of 3-(cyclopropyloxy)propan-1-ol and 5 mL of dichloromethane were added 1.2 mL of triethylamine and 1.3 g of p-toluenesulfonic acid chloride under ice-cooling, followed by stirring for 4 hours. The reaction mixture was diluted with chloroform, washed with 1 M hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 522 mg of 3-(cyclopropyloxy)propyl p-toluenesulfonate.

Workup

  1. temperaturecooling
  2. washwashed with 1 M hydrochloric acid
  3. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and saturated brine, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-620c11a65b82438e8e48d344fe5ec054
Source dataset
uspto-grants-2014_09
Patent number
US08822448B2

Reaction notes

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