tetrahydro-3,5-bis(phenylmethylene)-4H-thiopyran-4-one → 3,5-Dibenzylidene-1lambda~4~-thiane-1,4-dione

HRID 1576019

Reaktionsgleichung

Reaktionsgleichung von HRID 1576019
I([O-])(=O)(=O)=[O:2].[Na+].[C:7]1([CH:13]=[C:14]2[C:19](=[O:20])[C:18](=[CH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17][S:16][CH2:15]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>O.CO>[C:22]1([CH:21]=[C:18]2[C:19](=[O:20])[C:14](=[CH:13][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:15][S:16](=[O:2])[CH2:17]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Komponenten

5

Edukt 2

HCID 336779tetrahydro-3,5-bis(phenylmethylene)-4H-thiopyran-4-oneHCID 23667635Sodium periodate

Produkt 1

HCID 681371553,5-Dibenzylidene-1lambda~4~-thiane-1,4-dioneAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 10.4g of sodium periodate in 50ml of water is added to a suspension of 7.0g of tetrahydro-3,5-bis-(phenylmethylene)-4H-thiopyran-4-one in 300ml of methanol. The mixture is stirred at room temperature for 3 days (a water bath is used for the first hour to moderate a slightly exothermic reaction). Solvent is removed in vacuo and the residue is stirred with chloroform and filtered. The filtrate is concentrated in vacuo and the residue is crystallized from 150ml of methanol, giving 6.4g of the title compound, melting point 155°-160°C. A second crop of 0.5g of the title compound, melting point 154°-157°C is also obtained.

Aufarbeitung

  1. customa slightly exothermic reaction)
  2. customSolvent is removed in vacuo
  3. stirringthe residue is stirred with chloroform
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated in vacuo
  6. customthe residue is crystallized from 150ml of methanol

Quellen und Nachweise

ORD-Eintrag
ord-ef79094605584d78a57c1ca8d4284088
Quelldatensatz
uspto-grants-1976_09
Patentnummer
US03979381

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