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

HRID 718563Notes

Reaction equation

HRID 718563 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 mml) was added portion-wise. The resulting mixture was stirred at rt overnight. The reaction mixture was concentrated in vacuo 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 organic 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 in vacuo
  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 organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-956632bcd72b40a390d84a0875ce7e00
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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