Toluene → HCID 22790348, Verbindung

HRID 1077011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1077011
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][SH:9])[CH2:3][CH2:2]1.[Na].C1(C)C=CC=CC=1.Br[CH2:19][C:20](=[O:42])[C@@H:21]1[C@:38]2([CH3:39])[C@H:24]([C@H:25]3[C@H:35]([C:36](=[O:40])[CH2:37]2)[C@:33]2([CH3:34])[C@H:28]([CH2:29][C@H:30]([OH:41])[CH2:31][CH2:32]2)[CH2:27][CH2:26]3)[CH2:23][CH2:22]1>C(O)(C)C>[OH:41][C@@H:30]1[CH2:31][CH2:32][C@@:33]2([CH3:34])[C@@H:28]([CH2:27][CH2:26][C@@H:25]3[C@@H:35]2[C:36](=[O:40])[CH2:37][C@@:38]2([CH3:39])[C@H:24]3[CH2:23][CH2:22][C@@H:21]2[C:20](=[O:42])[CH2:19][S:9][CH2:8][CH2:7][N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH2:29]1

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 206664-MorpholineethanethiolHCID 5360545SodiumHCID 8673346721-Bromo-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Produkt 1

HCID 22790348HCID 22790348, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

2-Morpholinoethanethiol (1 ml.) was added to a warm solution of sodium (0.6 g.) in a mixture of dry toluene (30 ml.) and isopropyl alcohol (25 ml.). After 5 min., 21-bromo-3α-hydroxy-5α-pregnane-11,20-dione (2.0 g.) was added and the resulting mixture was stirred at 40° for 30 min. The mixture was then partitioned between water and ether and the organic layer was washed with water, dried (Na2SO4) and evaporated. The residue was subjected to preparative t.l.c. (EtOAc) to give title compound (150 mg.) as a white foam, [α]D + 73° (c 0.9); λmax. 243 nm. (ε 570).

Aufarbeitung

  1. customThe mixture was then partitioned between water and ether
  2. washthe organic layer was washed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-0a8db89dbfbc424897a7536b741265e8
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03959260

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