3,3-Bis(hydroxymethyl)-2,3-dihydro-4H-1-benzothiopyran-4-one → HCID 59756936, Verbindung

HRID 1009213Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009213
[OH:1][CH2:2][C:3]1([CH2:14][OH:15])[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[S:5][CH2:4]1.I([O-])(=O)(=O)=[O:17].[Na+]>CO.O>[OH:15][CH2:14][C:3]1([CH2:2][OH:1])[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[S:5](=[O:17])[CH2:4]1

Komponenten

5

Edukt 2

HCID 27640233,3-Bis(hydroxymethyl)-2,3-dihydro-4H-1-benzothiopyran-4-oneHCID 23667635Sodium periodate

Produkt 1

HCID 59756936HCID 59756936, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of 3,3-bis(hydroxymethyl)thiochroman-4-one (200 mg, 0.9 mmol) in MeOH (5 ml) was admixed with a solution of sodium metaperiodate (206 mg, 0.96 mmol) in water (2 ml) and stirred at RT for 72 h. The reaction mixture was diluted with water (10 ml) and extracted with EtOAc (3×30 ml), 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, EtOAc), the desired product was obtained as a white solid (113 mg, 52% of theory, m.p. 108-111° C.).

Aufarbeitung

  1. extractionextracted with EtOAc (3×30 ml)
  2. dry with materialthe combined organic phases were dried over sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customAfter column chromatography purification of the residue (silica gel, EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-42f50f003db94066851b14c10cd962e1
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973072B2

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