Pyridine → HCID 86736632, Verbindung

HRID 1855829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1855829
[OH:1][CH2:2][C@@H:3]1[C@@H:8]([CH2:9][OH:10])[CH:7]2[CH2:11][CH:4]1[CH2:5][CH2:6]2.N1C=CC=CC=1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>O>[S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)([OH:1])(=[O:26])=[O:25].[S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=1)([OH:1])(=[O:26])=[O:25].[OH:1][CH2:2][C@@H:3]1[C@@H:8]([CH2:9][OH:10])[CH:7]2[CH2:11][CH:4]1[CH2:5][CH2:6]2

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 57246542HCID 57246542, Verbindung

Produkt 1

HCID 86736632HCID 86736632, VerbindungAusbeute 223,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

In a 200 ml round bottom flask capped with a CaCl2 drying tube was placed 7.2 g (0.0461 moles) of (2S,3S)-2,3-bis(hydroxymethyl)bicyclo[2.2.1]heptane (m.p. 58° C.) together with 45 ml of pyridine and 18.4 g (0.096 moles) of p-toluenesulfonyl chloride. The mixture was cooled in an ice bath and stirred for 3 hours and then diluted with 10 ml of H2O. The precipitate which formed was filtered and washed to remove pyridine. The solid was recrystallized from ethanol to give 17.2 g (92%) of fine white needles, m.p. 100°-101° C., αD =+32.2° C.

Aufarbeitung

  1. customIn a 200 ml round bottom flask capped with a CaCl2 drying tube
  2. temperatureThe mixture was cooled in an ice bath
  3. customThe precipitate which formed
  4. filtrationwas filtered
  5. washwashed
  6. customto remove pyridine
  7. customThe solid was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-e93c5cb704984e3a97d0affec8c71bb9
Quelldatensatz
uspto-grants-1980_08
Patentnummer
US04216331

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