Potassium Carbonate → 1-Cyclobutanesulfonyl-naphthalene

HRID 2212064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2212064
[C:1]1(S)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH:12]1(Br)[CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[K+].C1OCCOCCOCCOCCOCCOC1.O[O:47][S:48]([O-:50])=O.[K+]>O.CC(C)=O.ClCCl.C(#N)C>[CH:12]1([S:48]([C:9]2[C:10]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[CH:6]=[CH:7][CH:8]=2)(=[O:50])=[O:47])[CH2:15][CH2:14][CH2:13]1

Komponenten

11

Edukt 6

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 682591-NaphthalenethiolHCID 78110BromocyclobutaneHCID 516893Potassium BicarbonateHCID 23707502Potassium hydroxy sulfite

Produkt 1

HCID 219637531-Cyclobutanesulfonyl-naphthaleneAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel2×HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of naphthalene-1-thiol (1.17 g, 7.3 mmol), cyclobutyl bromide (1.45 g, 10.7 mmol), potassium carbonate (1.06 g, 7.7 mmol) and acetonitrile (20 ml) was stirred at 70° C. for 40 hours. the mixture was poured into water and extracted into ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was treated with dichloromethane (30 ml), acetone (5 ml), 10% aqueous potassium bicarbonate and 18-crown-6 (100 mg, 0.4 mmol) and a solution of Oxone™ (10 g) in water (100 ml) was added. After completion, the layers were separated and the aqueous phase was extracted with dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified on silica (i-hexane-ethyl acetate) to give the title product (257 mg, 14%).

Aufarbeitung

  1. extractionextracted into ethyl acetate
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. customAfter completion, the layers were separated
  5. extractionthe aqueous phase was extracted with dichloromethane
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified on silica (i-hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-9f3055e764ae41d48e80290051e6bc57
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07101892B2

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