Sulfuric Acid → Estra-1,3,5(10),16-tetraen-3-ol

HRID 1957097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1957097
[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C:7](=[CH:8][CH2:9][C:10]4[CH:11]=[C:12]([OH:19])[CH:13]=[CH:14][C:15]=43)[C@@H:6]1[CH2:5][CH2:4][CH2:3]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].OS(O)(=O)=O>CCOCC>[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C@@H:7]([CH2:8][CH2:9][C:10]4[CH:11]=[C:12]([OH:19])[CH:13]=[CH:14][C:15]=43)[C@@H:6]1[CH2:5][CH:4]=[CH:3]2

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 15870996Estra-1,3,5(10),7-tetraen-3-olHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 101988Estra-1,3,5(10),16-tetraen-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

This synthesis is depicted in FIG. 11. A solution of the ketone 10 (800 mg, 3.10 mmol) in dry ether (5 ml) was added dropwise at RT. to a slurry of LiAlH4 (38 mg, 1 mmol) in ether (3 ml) (e). After 1 h, the mixture was hydrolyzed with 10% aq. H2SO4. After workup (ether), the crude product (802 mg, 9:1-mixture of 12 and 11) was chromatographed on silica gel with CH2Cl2. A small fraction of 11 (70 mg) was eluted first, followed by the main fraction of 12 (705 mg, 87%). M.p. 113°-115°, [a]- +36.3° (C=1.0). - IR. (CHCl3): 3640 m, 3500 br., 1585w. -1H-NMR. (90 MHz) : 0.78 (s, 3 H); 3.60 (m, w1/2 ≈(m, 20, 1 H); 5.71 (m, 1 H), 5.87 (m, 1 H).

Aufarbeitung

  1. customAfter workup (ether), the crude product (802 mg, 9:1-mixture of 12 and 11) was chromatographed on silica gel with CH2Cl2
  2. washA small fraction of 11 (70 mg) was eluted first
  3. custom+36.3° (C=1.0)

Quellen und Nachweise

ORD-Eintrag
ord-e61ddd4523ea4f64b0fcd76fbeb84758
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05783571

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