Ethyl Acetate → HCID 70565263, compound

HRID 126669Notes

Reaction equation

HRID 126669 reaction equation
[CH2:1]1[CH2:29][O:28][C@@:27]23[C@:22]([CH3:30])([CH2:23][CH2:24][CH2:25][CH2:26]2)[C@@H:21]2[C@H:5]([C@H:6]4[C@:18]([CH3:31])([CH2:19][CH2:20]2)[C@@H:9]([C@H:10]([CH3:17])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:8][CH2:7]4)[CH2:4][CH:3]3[O:2]1.C(OCC)(=[O:34])C>N1C=CC=CC=1>[CH2:1]1[CH2:29][O:28][C:3]2([C@@H:27]3[C@:22]([CH3:30])([CH2:23][CH2:24][C:25](=[O:34])[CH2:26]3)[C@@H:21]3[C@H:5]([C@H:6]4[C@:18]([CH3:31])([CH2:19][CH2:20]3)[C@@H:9]([C@H:10]([CH3:17])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:15])[CH3:16])[CH2:8][CH2:7]4)[CH2:4]2)[O:2]1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 86737521HCID 86737521, compound

Product 1

HCID 70565263HCID 70565263, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 6-ethylenedioxy-5α-cholestan-3β-(3, 12.5 g) in pyridine was added to ice-cold pyridine-CrO3 complex prepared by adding CrO3 (182 g) to ice-cold pyridine (182 ml). An additional amount of pyridine (90 ml) was utilized for complete transfer. The mixture was allowed to come to room temperature and stirred for 10 hr. It was then brought to a volume of 500 ml with ethyl acetate and filtered through a column packed with Celite (a diatomaceous silica product marketed by Johns-Manville Co.) (50 g, 4 cm diameter) slurried in ethyl acetate. Material eluted with a total of 750 ml of ethyl acetate was collected, and filtered through a 6 cm column packed with alumina (100 g) slurried in ethyl acetate. After elution with 1200 ml of ethyl acetate and evaporation of the solvent, a greenish solid was recovered. This was applied to a 2×23.5 cm (50 g alumina, AG-7 minus 200 mesh) column and eluted with ethyl acetate. The first 150 ml of eluant gave 12.3 g (98%) of pure 6,6-ethylenedioxy-5α-cholestan-3-one (4). An analytical sample recrystallized from MeOH was obtained as white crystals: m.p. 115°-116°; nmr (CDCl3) δ 2.35 (m, C-2 and C-4 protons), 3.9 (m, ketal); ir (KBr) 1710 cm+1 (C=O); mass spectrum: m/e 444 (M+, 19%, C29H48O3 : C, 78.33; H, 10.88; obs: C, 78.37; H, 10.93.

Workup

  1. customprepared
  2. customto come to room temperature
  3. filtrationfiltered through a column
  4. washMaterial eluted with a total of 750 ml of ethyl acetate
  5. customwas collected
  6. filtrationfiltered through a 6 cm column
  7. washAfter elution
  8. customwith 1200 ml of ethyl acetate and evaporation of the solvent
  9. customa greenish solid was recovered
  10. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-02b6892f506b4e9b846b2395eece5ced
Source dataset
uspto-grants-1981_03
Patent number
USRE030538

Reaction notes

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