Acetone → HCID 86733470, Verbindung

HRID 1077012Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1077012
[O:1]1[CH2:6][CH2:5][N:4]([CH:7](O)[CH3:8])[CH2:3][CH2:2]1.[Na].[C:11](=[S:13])=[S:12].Br[CH2:15][C:16](=[O:38])[C@@H:17]1[C@:34]2([CH3:35])[C@H:20]([C@H:21]3[C@H:31]([C:32](=[O:36])[CH2:33]2)[C@:29]2([CH3:30])[C@H:24]([CH2:25][C@H:26]([OH:37])[CH2:27][CH2:28]2)[CH2:23][CH2:22]3)[CH2:19][CH2:18]1.CC(C)=[O:41]>C1(C)C=CC=CC=1>[OH:37][C@@H:26]1[CH2:27][CH2:28][C@@:29]2([CH3:30])[C@@H:24]([CH2:23][CH2:22][C@@H:21]3[C@@H:31]2[C:32](=[O:36])[CH2:33][C@@:34]2([CH3:35])[C@H:20]3[CH2:19][CH2:18][C@@H:17]2[C:16](=[O:38])[CH2:15][S:12][C:11]([O:41][CH2:8][CH2:7][N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[S:13])[CH2:25]1

Komponenten

7

Edukt 5

HCID 180AcetoneHCID 6348Carbon DisulfideHCID 30293761-MorpholinoethanolHCID 5360545SodiumHCID 86733467HCID 86733467, Verbindung

Produkt 1

HCID 86733470HCID 86733470, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of morpholinoethanol (3.3 g., 2.5 mmole), dry toluene (50 ml.) and sodium (0.6 g.) was refluxed under nitrogen for 6 hr. and then left at room temperature for two days. The unreacted sodium was then removed and carbon disulphide (4 ml., 5.3 mmole) was added cautiously and the resulting mixture was allowed to stand at room temperature for 2 hr. The precipitated solid was collected rapidly by filtration and added immediately to a solution of 21-bromo-3α-hydroxy-5α-pregnane-11,20-dione (1.0 g., 2.3 mmole) in acetone. The resulting suspension was refluxed for 15 min. and then partitioned between water and ether. The organic layer was washed with water, dried (Na2SO4) and evaporated. The residue (900 mg.) was purified by preparative t.l.c. (EtOAc/petrol 1:1) to give title compound (0.35 g.) as a white foam, [α]D + 77° (c 1.2).

Aufarbeitung

  1. temperaturewas refluxed under nitrogen for 6 hr
  2. customThe unreacted sodium was then removed
  3. waitto stand at room temperature for 2 hr
  4. filtrationThe precipitated solid was collected rapidly by filtration
  5. temperatureThe resulting suspension was refluxed for 15 min.
  6. custompartitioned between water and ether
  7. washThe organic layer was washed with water
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customThe residue (900 mg.) was purified by preparative t.l.c

Quellen und Nachweise

ORD-Eintrag
ord-a611ccf9052241c4b8610025efd0c67a
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03959260

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