Tetrahydrofuran → HCID 53978241, Verbindung

HRID 1684565Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1684565
[F:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][CH2:5][Mg]Br.[CH3:10][C@:11]12[CH2:28][CH2:27][C@H:26]3[C@@H:16]([CH2:17][CH:18]=[C:19]4[C@:24]3([CH3:25])[CH2:23][CH2:22][C:21]([CH2:29][OH:30])=[CH:20]4)[C@@H:15]1[CH2:14][CH2:13][CH2:12]2.C1C[O:34][CH2:33]C1>>[F:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][CH2:5][CH:33]([C@H:12]1[CH2:13][CH2:14][C@H:15]2[C@H:16]3[C@H:26]([CH2:27][CH2:28][C@:11]12[CH3:10])[C@:24]1([CH3:25])[C:19]([CH:20]=[C:21]([CH2:29][OH:30])[CH2:22][CH2:23]1)=[CH:18][CH2:17]3)[OH:34]

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 86751003HCID 86751003, VerbindungHCID 178506316HCID 178506316, Verbindung

Produkt 1

HCID 53978241HCID 53978241, Verbindung

Versuchsvorschrift

4,4,4-trifluorobutyl magnesium bromide (0.25M in THF, 4.0 ml, 1.0 mmol) was added to a solution of (17β)-17-carboxaldehydo- androsta-3,5-diene-3-methanol (50 mg, 0.16 mmol) in THF at 0 degrees C. After 0.5 h the reaction was quenched with aqueous ammonium chloride, the aqueous layer was extracted with EtOAc, the combined organic extracts were dried (MgSO4), filtered, concentrated, and chromatographed (silica gel, 20% EtOAc) to yield the title compound.

Aufarbeitung

  1. customAfter 0.5 h the reaction was quenched with aqueous ammonium chloride
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialthe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed (silica gel, 20% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-788930b7e40e45a09fef5e4d8b2a9171
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05641765

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