Ethylene Glycol → 3-Hydroxy-5beta-estran-17-one ethylene ketal

HRID 7412

Reaktionsgleichung

Reaktionsgleichung von HRID 7412
[OH:1][CH:2]1[CH2:19][CH2:18][C@H:17]2[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:20])[CH2:3]1.[CH2:21](O)[CH2:22][OH:23].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CCOC(C)=O.CCCCCC>C1C=CC=CC=1.CCOC(C)=O>[CH2:22]1[O:23][C:11]2([CH2:10][CH2:9][C@H:8]3[C@H:7]4[C@H:16]([CH2:15][CH2:14][C@:12]23[CH3:13])[C@@H:17]2[C@@H:4]([CH2:3][CH:2]([OH:1])[CH2:19][CH2:18]2)[CH2:5][CH2:6]4)[O:20][CH2:21]1

Komponenten

7

Edukt 4

HCID 174Ethylene GlycolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 21226206Ethyl acetate hexaneHCID 227956593-Hydroxy-5betaestran-17-one

Produkt 1

HCID 867601793-Hydroxy-5beta-estran-17-one ethylene ketalAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Compound 4(10 g, 36.2 mmol) was dissolved in dry benzene (150 ml) mixed with ethylene glycol (25 ml, 280 mmol) and pyridinium p-toluenesulfonate (1 g, 3.9 mmol) and refluxed using a Dean-stark separator overnight till no starting material was detected by TLC. The cold solution was diluted with EtOAc (100 ml), washed twice with brine, dried on Na2SO4 and the solvents removed under reduced pressure. Flash-chromatography on silica gel with EtOAc: Hexane 4:6 as eluant to give 11.0 g (94.5% yield) the title compound as a white solid.

Aufarbeitung

  1. temperaturerefluxed
  2. washwashed twice with brine
  3. customdried on Na2SO4
  4. customthe solvents removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-faa2f348d6f5478eb5c5bd468fd5e72f
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087590B2

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