Triethylamine → HCID 67739305, Verbindung

HRID 486859Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 486859
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C@@H:19]1[C@H:14]([CH2:15][C:16](=[O:23])[CH2:17][CH2:18]1)[CH2:13][CH2:12]3)(=[O:3])[CH3:2].C(N(CC)CC)C.O([Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])S(C(F)(F)F)(=O)=O>ClCCl>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C@@H:19]1[C@H:14]([CH2:15][CH:16]([O:23][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])[CH2:17][CH2:18]1)[CH2:13][CH2:12]3)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 24213233767-87-2

Produkt 1

HCID 67739305HCID 67739305, VerbindungAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 17β-acetyloxy-5α-estran-3-one (1.595 g, 5 mmol) in dry dichloromethane (30 mL) was added with stirring at ice-water bath temperature, triethyl amine (2 mL) followed by t-butyldimethylsilyl triflate (2.64 g, 10 mmol). The solution was stirred for 25 min, then diluted with dichloromethane (20 mL) and washed with satd.aq. NaHCO3 (30 mL), brine (30 mL) and dried over Na2SO4. The solvent was removed to yield a solid, which was purified by chromatography (silica gel, dichloromethane, pretreated with 1% triethyl amine in hexanes) to get 1.9 g (87%) of pure product as colorless crystals, m.p. 89°-90° C.

Aufarbeitung

  1. washwashed with satd.aq
  2. dry with materialNaHCO3 (30 mL), brine (30 mL) and dried over Na2SO4
  3. customThe solvent was removed
  4. customto yield a solid, which
  5. customwas purified by chromatography (silica gel, dichloromethane, pretreated with 1% triethyl amine in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3a9459dedd2743a9a20acf6a42b7d205
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05292906

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