Benzoyl chloride → 3beta,25-Dibenzoyloxycholest-5-ene

HRID 1834202

Reaktionsgleichung

Reaktionsgleichung von HRID 1834202
[OH:1][C:2]([CH2:5][CH2:6][CH2:7][C@H:8]([C@@H:10]1[C@:28]2([CH3:29])[C@H:13]([C@H:14]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:17]([CH2:18][C@H:19]([CH2:21][CH2:22]2)[OH:20])=[CH:16][CH2:15]3)[CH2:12][CH2:11]1)[CH3:9])([CH3:4])[CH3:3].[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>N1C=CC=CC=1>[C:30]([O:20][C@H:19]1[CH2:21][CH2:22][C@@:23]2([CH3:24])[C:17](=[CH:16][CH2:15][C@@H:14]3[C@@H:25]2[CH2:26][CH2:27][C@@:28]2([CH3:29])[C@H:13]3[CH2:12][CH2:11][C@@H:10]2[C@H:8]([CH3:9])[CH2:7][CH2:6][CH2:5][C:2]([O:1][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([CH3:3])[CH3:4])[CH2:18]1)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Komponenten

4

Edukt 2

HCID 7412Benzoyl chloride2×HCID 6509425-Hydroxycholesterol

Produkt 1

HCID 155418583beta,25-Dibenzoyloxycholest-5-ene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Heat 2.9 gm. (7.2 mmole) of 25-hydroxycholesterol with 2.1 ml. (18 mmole) of benzoyl chloride in 30 ml. of pyridine at 70°-80° C. for 4 hours. Add an additional 1.4 ml. (12 mmole) of benzoyl chloride and continue heating at 75°-80° C. for 1 hour. Pour the reaction mixture into ice-water mixture (b 1:1, 500 gm.) Stir for 1 hour, separate the precipitate and wash with ice-water. Recrystalize from acetone. Dissolve the crude product (3.8 gm.) in methylene chloride-hexane (3:2, 40 ml.) and pass the solution through a silica gel column (120 gm.). Elute the column with 800 ml. methylene chloride-hexane (5:1) followed by 800 ml. methylene chloridehexane (10:1). Combine the fractions and concentrate to a residue. Recrystalize from acetone to obtain the pure product (3.32 gm., m.p. 130°-132° C.).

Aufarbeitung

  1. temperatureHeat 2.9 gm
  2. additionAdd an additional 1.4 ml
  3. customseparate the precipitate
  4. washwash with ice-water
  5. customRecrystalize from acetone
  6. dissolutionDissolve the crude product (3.8 gm.) in methylene chloride-hexane (3:2, 40 ml.)
  7. washElute the column with 800 ml
  8. concentrationCombine the fractions and concentrate to a residue
  9. customRecrystalize from acetone
  10. customto obtain the pure product (3.32 gm., m.p. 130°-132° C.)

Quellen und Nachweise

ORD-Eintrag
ord-61fc24653fa845419c52b3cb002285b2
Quelldatensatz
uspto-grants-1978_01
Patentnummer
US04069321

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