Reaktion #213852

ord-97c691727a954e0a8b007c3fcd9db61e

Reaktionsgleichung

CC(=O)O.CC(=O)O.CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C
1α-hydroxycholesterol diacetate
[K+].[OH-]
KOH
CC(=O)O
acetic acid
O
water
→
CC(=O)O[C@H]1C[C@H](O)CC2=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@@H]3[C@]21C
1α-acetoxycholesterol
Ausbeute 107.8%

Edukte

CC(=O)O.CC(=O)O.CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C
1α-hydroxycholesterol diacetate
[K+].[OH-]
KOH
CC(=O)O
acetic acid
O
water

Reagenzien

Keine

Lösungsmittel

CCOCC
diethyl ether
CO
methanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONwas added slowly
  2. 2
    workup.STIRRINGAfter stirring for 2.5 hours
  3. 3
    Extraktionthe mixture was extracted with ether (3×)
  4. 4
    Trocknenwere dried (Na2SO4)
  5. 5
    Sonstigeevaporated to dryness

Vorschrift

A solution of 600 mg of 1α-hydroxycholesterol diacetate (16) in 1.6 ml of diethyl ether was cooled to ice-bath temperature and 1.6 ml of 0.1 N KOH in methanol was added slowly with stirring. After stirring for 2.5 hours, acetic acid (0.25 ml) and water was added, the mixture was extracted with ether (3×), combined extracts were dried (Na2SO4) and evaporated to dryness to give 0.55 g of 1α-acetoxycholesterol (17), homogeneous on tlc. nmr (CDCl3) δ5.55 (1H, broad, C-6), 5.00 (1H, m, C-1), 3.62 (1H, m, C-3), 2.10 (3H, s, OAc).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: USRE030538uspto-grants-1981_03