Formaldehyde → 3,3-Bis(hydroxymethyl)-2,3-dihydro-4H-1-benzothiopyran-4-one

HRID 1009211Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009211
[S:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.[CH2:12]=[O:13].[C:14](=[O:17])([O-])[O-].[K+].[K+]>CO.O>[OH:13][CH2:12][C:3]1([CH2:14][OH:17])[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[S:1][CH2:2]1

Komponenten

6

Edukt 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 19048Thiochroman-4-one

Produkt 1

HCID 27640233,3-Bis(hydroxymethyl)-2,3-dihydro-4H-1-benzothiopyran-4-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A solution of thiochroman-4-one (2.0 g, 12 mmol) in MeOH (40 ml) and water (8 ml) was admixed with 35% eq. formalin solution (8 ml) and potassium carbonate (200 mg). The reaction mixture was stirred at 40° C. for 2 h and then at RT for 2 h, the solvent was removed under reduced pressure and the residue was admixed with water. The aqueous solution was extracted repeatedly with EtOAc, the combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. After column chromatography purification of the residue (silica gel, 1:1 cyclohexane/EtOAc), the desired product was obtained as a white solid (1.71 g, 63% of theory, m.p. 136-139° C.).

Aufarbeitung

  1. waitat RT for 2 h
  2. customthe solvent was removed under reduced pressure
  3. extractionThe aqueous solution was extracted repeatedly with EtOAc
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customAfter column chromatography purification of the residue (silica gel, 1:1 cyclohexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-237e216f9c534e61a207f2d196d474de
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973072B2

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