Ethyl Acetate → Butyl 3-oxocyclobutane-1-sulfonate

HRID 1259401Notes

Reaction equation

HRID 1259401 reaction equation
[Cr]([O-])(OCl)(=O)=O.[NH+]1C=CC=CC=1.[OH:13][CH:14]1[CH2:17][CH:16]([S:18]([O:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:20])=[O:19])[CH2:15]1.C(OCC)(=O)C>C(Cl)Cl.CCCCCC>[O:13]=[C:14]1[CH2:17][CH:16]([S:18]([O:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:20])=[O:19])[CH2:15]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 86656333Butyl 3-hydroxycyclobutane-1-sulfonateHCID 178526120HCID 178526120, compound

Product 1

HCID 58380588Butyl 3-oxocyclobutane-1-sulfonateYield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

Pyridinium chloro chromate (10.3 g, 48.07 mmol) was added to a cooled solution of butyl 3-hydroxycyclobutane-1-sulfonate (5 g, 24.03 mmol) in dry DCM (50 mL) at 0° C. The resulting reaction mixture was stirred at room temperature overnight. The reaction was monitored by TLC (40% ethyl acetate in hexane). The reaction mixture was diluted with DCM, filtered and the filtrate was concentrated to afford the crude product. Purification by column chromatography on silica gel (15% ethyl acetate in hexane) afforded 2.8 g of the product (58% yield).

Workup

  1. customThe resulting reaction mixture
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated
  4. customto afford the crude product
  5. customPurification by column chromatography on silica gel (15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-96f4d10f457a4a418fd500b639a81a1b
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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