Hydrochloric Acid → HCID 11022977, Verbindung

HRID 1357477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1357477
CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[CH3:15][O:16][C:17]1[C:18]([OH:36])=[CH:19][C:20]2[CH2:21][CH:22]=[C:23]3[C@@H:32]([C:33]=2[CH:34]=1)[CH2:31][CH2:30][C@@:28]1([CH3:29])[C@H:24]3[CH2:25][CH2:26][C:27]1=[O:35].Cl>C1COCC1.CO.[OH-].[K+].OO.O>[CH3:15][O:16][C:17]1[C:18]([OH:36])=[CH:19][C:20]2[CH2:21][CH:22]=[C:23]3[C@@H:32]([C:33]=2[CH:34]=1)[CH2:31][CH2:30][C@@:28]1([CH3:29])[C@H:24]3[CH2:25][CH2:26][C@@H:27]1[OH:35]

Komponenten

9

Edukt 3

HCID 313Hydrochloric AcidHCID 30827972-MethoxyequilinHCID 3611392Lithium tri-s-butylborohydride

Produkt 1

HCID 11022977HCID 11022977, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 784Hydrogen PeroxideKatalysatorHCID 887MethanolKatalysatorHCID 14797Potassium HydroxideKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Under nitrogen, a solution of L-Selectride in THF (1 M, 0.081 mL, 0.081 mmol) was added dropwise to a solution of 2-methoxy-3-hydroxyestra-1,3,5(10),7-tetraen-17-one (19) (0.008 g, 0.027 mmol) in dry THF (1.0 mL) cooled to 0° C. in an ice bath. The reaction was allowed to warm to room temperature and stirred for 45 m. Methanol (3 drops) followed by methanolic KOH (3%, 3 drops) were added and the mixture was cooled to 0° C. in an ice bath. Hydrogen peroxide solution (30%, 5 drops) was added and the mixture was allowed to warm to room temperature. The reaction was diluted with water, acidified with HCl, and extracted with methylene chloride (3x). The organic fractions were washed with water (1x) and brine (1x), filtered through sodium sulfate, combined and concentrated in vacuo to give 0.006 g residue. This material was crystallized from ether/hexanes to give the purified product (20) (0.0037 g, 45.9%). NMR (300 MHz, CDCl3) δ 0.662 (s, 18-CH3), 3.376 (m, 17-H), 3.867 (s, 2-OMe), 5.402 (t, J=1.65 Hz, 7-H), 6.662 (s, 4-H), 6.692 (s, 1-H) ppm. Analysis Calc. for Cl9H24O3

Aufarbeitung

  1. temperatureto warm to room temperature
  2. additionwere added
  3. temperaturethe mixture was cooled to 0° C. in an ice bath
  4. temperatureto warm to room temperature
  5. extractionextracted with methylene chloride (3x)
  6. washThe organic fractions were washed with water (1x) and brine (1x)
  7. filtrationfiltered through sodium sulfate
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-72826e7346104ef5be65477519e121b8
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593321B2

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