Oxalic Acid → HCID 131724378, Verbindung

HRID 49410Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 49410
CO[C:3]1[CH2:4][C:5]2[CH2:6][C@@H:7]([CH3:24])[C@@H:8]3[C@@H:17]([C:18]=2[CH2:19][CH:20]=1)[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@:9]23[CH2:23][C@@H:10]2[CH2:11][C@H:12]1[CH2:21]O.C(O)(=O)[C:26](O)=[O:27].C(=O)([O-])[OH:32].[Na+]>CO.O1CCCC1.O>[OH:27][CH2:26][CH2:21][C@@H:12]1[CH2:11][C@H:10]2[CH2:23][C@@:9]32[C@H:8]2[C@H:17]([CH2:16][CH2:15][C@:13]13[CH3:14])[C:18]1[CH2:19][CH2:20][C:3](=[O:32])[CH2:4][C:5]=1[CH2:6][C@H:7]2[CH3:24]

Komponenten

7

Edukt 3

HCID 971Oxalic AcidHCID 516892Sodium BicarbonateHCID 69625019(7alpha,14beta,15beta,17alpha)-3-Methoxy-7-methyl-14,15-methyleneestra-2,5(10)-diene-17-methanol

Produkt 1

HCID 131724378HCID 131724378, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of (7α,14β,15β,17α)-3-methoxy-7-methyl-14,15-methyleneestra-2,5(10)-diene-17-methanol (Example 1, step vi; 7.38 g) in a mixture of methanol (68 ml) and tetrahydrofuran (48 ml) was treated with a solution of oxalic acid (2.38 g) in water (40 ml). After 1 h stirring at room temperature, the reaction mixture was poured into a saturated aqueous solution of sodium hydrogencarbonate and the product was extracted into ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography afforded (7α,14β,15β,17α)-17-(hydroxyethyl)-7-methyl-14,15-methyleneestr-5(10)-en-3-one (4.27 g). 1H NMR (CDCl3) δ3.69 (m, 1H), 3.51 (t, 1H, J=9.0 Hz), 2.72 (bs, 2H), 2.46 (bs, 2H), 1.04 (s, 3H), 0.69 (d, 3H, J=7.1 Hz), 0.48(dd, 1H, J=8.3 and 5.1 Hz), 0.27 (dd, 1H, J=5.1 and 3.1 Hz).

Aufarbeitung

  1. extractionthe product was extracted into ethyl acetate
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d3ce938e8ba948cdb819560530d83ab7
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706700B2

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