Water → 7-(Methylsulfanyl)-9H-xanthene-3-carbaldehyde

HRID 1199726Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1199726
C(Cl)(=O)C(Cl)=O.[CH3:7][S:8][C:9]1[CH:22]=[CH:21][C:20]2[O:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:23][OH:24])[CH:17]=3)[CH2:12][C:11]=2[CH:10]=1.C(N(CC)CC)C.O>C(Cl)Cl.CS(C)=O.C(OCC)(=O)C>[CH3:7][S:8][C:9]1[CH:22]=[CH:21][C:20]2[O:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH:23]=[O:24])[CH:17]=3)[CH2:12][C:11]=2[CH:10]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19865558[7-(Methylsulfanyl)-9H-xanthen-3-YL]methanol

Produkt 1

HCID 198655577-(Methylsulfanyl)-9H-xanthene-3-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under dry nitrogen, dimethylsulphoxide (5 ml) was added dropwise to a stirred solution of oxalyl chloride (0.89 ml) in methylene chloride (5 ml) at -60° C. After 2 minutes a solution of the xanthene from step (A) (2.3 g) in dimethylsulphoxide (35 ml) was introduced dropwise over 5 minutes whilst maintaining the temperature below -50° C. with cooling. After 15 minutes triethylamine (6.20 ml) was added, the mixture allowed to warm to room temperature and then poured into water. The mixture was ethyl acetate extracted, the organic layers were combined, washed with brine, dried over magnesium sulphate and evaporated yielding the title carboxaldehyde (1.97 g), m.p. 122°-123° C.

Aufarbeitung

  1. temperaturewhilst maintaining the temperature below -50° C.
  2. temperaturewith cooling
  3. extractionextracted
  4. washwashed with brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customyielding the title carboxaldehyde (1.97 g), m.p. 122°-123° C.

Quellen und Nachweise

ORD-Eintrag
ord-010d55eb04834467b77a1d56a9e94278
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04902701

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