Hydrochloric Acid → Phenyl(tetrahydro-2H-thiopyran-4-yl)methanone

HRID 900761

Reaktionsgleichung

Reaktionsgleichung von HRID 900761
[S:1]1[CH2:6][CH2:5][CH:4]([C:7]#N)[CH2:3][CH2:2]1.[C:9]1([Mg]Br)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CC[O:19]CC.Cl>C1COCC1.[Cu]I>[C:9]1([C:7]([CH:4]2[CH2:5][CH2:6][S:1][CH2:2][CH2:3]2)=[O:19])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 21598641Thiane-4-carbonitrileHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 69290818Phenyl(tetrahydro-2H-thiopyran-4-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Tetrahydro-2H-thiopyran-4-carbonitrile (2.6 g, 20.5 mmol) and CuI (195 mg, 1 mmol) were diluted in dry THF (200 ml). A 1M solution of phenyl magnesium bromide in THF (41 ml, 41 mmol) was added and the mixture was heated at reflux for 16 hours. After cooling at room temperature, ether was added and the imine was hydrolyzed with a 1 N HCl solution for 10 minutes. The organic phase was separated and treated with a 0.1 N HCl solution for 10 minutes. The organic phase was separated and washed with brine, dried over MgSO4 and evaporated in vacuum. After chromatography on silica gel (CH2Cl2/hexane 30/70), the phenyl(tetrahydro-2H-thiopyran-4-yl)methanone 17 was obtained as a white solid (3 g, 70%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 hours
  3. customThe organic phase was separated
  4. additiontreated with a 0.1 N HCl solution for 10 minutes
  5. customThe organic phase was separated
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. customevaporated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-dfd66986ba0d4db5a9580e8fab9bfee8
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361668B2

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