4-Toluenesulfonyl chloride → Ethyl 3-(tosyloxy)cyclobutane-1-carboxylate

HRID 1772679Notes

Reaction equation

HRID 1772679 reaction equation
[OH:1][CH:2]1[CH2:5][CH:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3]1.[S:11](Cl)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12]>N1C=CC=CC=1.CCOC(C)=O>[S:11]([O:1][CH:2]1[CH2:5][CH:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3]1)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 21716982Ethyl 3-hydroxycyclobutane-1-carboxylate

Product 1

HCID 57478426Ethyl 3-(tosyloxy)cyclobutane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 3-hydroxycyclobutanecarboxylate (10.2 g, 78.4 mmol) in dry pyridine (56.5 mL) at 0° C., TsCl (14.9 g, 78.4 mmol) was added portionwise. The resulting mixture was stirred at rt overnight. The reaction mixture was concentrated under reduced pressure and the residue obtained was dissolved in EtOAc (100 mL) and sequentially washed with 2 N HCl (100 mL), saturated NaHCO3 (100 mL) and water (100 mL). The EtOAc layer was dried over Na2SO4, filtered, and concentrated to obtain ethyl 3-(tosyloxy)cyclobutanecarboxylate as a pale yellow oil, which was used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue obtained
  3. washsequentially washed with 2 N HCl (100 mL), saturated NaHCO3 (100 mL) and water (100 mL)
  4. dry with materialThe EtOAc layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-94c4518beadd41b28b79976728de0385
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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