Hydrochloric Acid → 69140-15-4

HRID 479304Notes

Reaction equation

HRID 479304 reaction equation
C([O:4][C@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@@H:7]([CH2:8][C:9](=[O:32])[C:10]3[C@H:11]4[C@:23]([CH3:31])([CH2:24][CH2:25][C:26]=32)[C@@H:14]([C@H:15]([CH3:22])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:13][CH2:12]4)[CH2:6]1)(=O)C.Cl.O>C(O)C.[OH-].[Na+]>[O:32]=[C:9]1[CH2:8][C@@H:7]2[C@:27]([CH3:30])([CH2:28][CH2:29][C@H:5]([OH:4])[CH2:6]2)[C:26]2[CH2:25][CH2:24][C@@:23]3([CH3:31])[C@@H:11]([CH2:12][CH2:13][C@@H:14]3[C@H:15]([CH3:22])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[C:10]1=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 57120710HCID 57120710, compound

Product 1

HCID 2112115569140-15-4Yield 43.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

0.50 g of 3β-acetoxy-7-oxo-5α-cholest-8-ene (Fieser, L F J Am Chem Soc (1953) 4395) was refluxed in a mixture of 30 ml of ethanol and 20 ml of 1 M aqueous sodium hydroxide for 1 hour. After cooling to room temperature, 23 ml of 1M hydrochloric acid and 100 ml of water were added. After cooling on an ice bath, the precipitate was filtered off, washed with water and dried to give 0.435 g of the crude compound which was purified by chromatography on silica gel (methylene chloride/methanol, 40:1 (w/w)) and crystallized from methanol/water to give 0.198 g of the title compound. Melting point: 115-117° C. The 1H-NMR spectrum (CDCl3,d) showed characteristic signals at: 0.59 (s,3H); 1.18 (s,3H); 3.64 (m,1H). The 13C-NMR spectrum (CDCl3, 100.6 MHz) showed characteristic signals at: 69.5; 132.8; 164.8; 198.6.

Workup

  1. temperatureAfter cooling on an ice bath
  2. filtrationthe precipitate was filtered off
  3. washwashed with water
  4. customdried
  5. customto give 0.435 g of the crude compound which
  6. customwas purified by chromatography on silica gel (methylene chloride/methanol, 40:1 (w/w))
  7. customcrystallized from methanol/water

Sources & evidence

ORD record
ord-65c3a6ea20e443ceb040c0e6b4481a69
Source dataset
uspto-grants-2003_11
Patent number
US06645953B2

Reaction notes

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