Oxalyl chloride → 4H-[1]-Benzothiopyrano[4,3-b]furan-2,3-dione

HRID 1607922Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1607922
C[Si](C)(C)[O:3][C:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7][CH2:6][CH:5]=1.[C:16](Cl)(=[O:20])[C:17](Cl)=[O:18]>CCOCC>[O:3]1[C:17](=[O:18])[C:16](=[O:20])[C:5]2[CH2:6][S:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:4]1=2

Komponenten

4

Edukt 2

HCID 65578Oxalyl chlorideHCID 127939784-[trimethyl[silyl]oxy]-2H-benzothiopyran

Produkt 1

HCID 142558494H-[1]-Benzothiopyrano[4,3-b]furan-2,3-dioneAusbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a stirred mixture of 4-[trimethyl[silyl]oxy]-2H-benzothiopyran (380.5 g,1.609 mol), prepared according to the method of L. Hellberg et al, Tet. Letters, 3553-3554 (1974), and one liter of diethyl ether, were added 103.8 g (0.818 mol) of oxalyl chloride in a dropwise manner over a period of 50 minutes at room temperature under nitrogen. The mixture was stirred at room temperature for 17 hours after which time the ether was removed under reduced pressure. The residue was triturated with isopropyl ether/hexane to give 146.9 g (82.3%) of a brown crystalline solid, mp 156° C. (dec).

Aufarbeitung

  1. customprepared
  2. customwas removed under reduced pressure
  3. customThe residue was triturated with isopropyl ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-b1257e3dde76447a93b2a762a3f0143b
Quelldatensatz
uspto-grants-1989_09
Patentnummer
US04868200

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