Ethyl Acetate → Potassium 3-(benzyloxy)cyclobutane-1-sulfonate

HRID 1259429Notes

Reaction equation

HRID 1259429 reaction equation
C([S-])#N.[K+:4].[CH2:5]([O:12][CH:13]1[CH2:16][CH:15]([S:17]([O:20]CCCC)(=[O:19])=[O:18])[CH2:14]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(OCC)(=O)C>COCCOC.O.CCCCCC>[CH2:5]([O:12][CH:13]1[CH2:14][CH:15]([S:17]([O-:20])(=[O:19])=[O:18])[CH2:16]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[K+:4]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 516872Potassium thiocyanateHCID 58380564Butyl 3-(benzyloxy)cyclobutane-1-sulfonate

Product 1

HCID 86656336Potassium 3-(benzyloxy)cyclobutane-1-sulfonateYield 70%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

KSCN (68 mg, 0.66 mmol) and butyl 3-(benzyloxy)cyclobutane-1-sulfonate (0.18 g, 0.604 mmol) in DME-water mixture (1:1 ratio, 4 mL) were heated at 85° C. overnight. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mass was concentrated under reduced pressure and the crude residue obtained was washed with ether to afford 0.11 g of the product (70% yield).

Workup

  1. concentrationThe reaction mass was concentrated under reduced pressure
  2. customthe crude residue obtained
  3. washwas washed with ether

Sources & evidence

ORD record
ord-0b927242a0634ce6a0441bcdf72315dc
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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