Hydrochloric Acid → 3beta, 5alpha,25-Tri-hydroxy-cholestane

HRID 1658418Notes

Reaction equation

HRID 1658418 reaction equation
C([O:4][C@H:5]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C@@:7]([OH:33])([CH2:8][CH2:9][C@@H:10]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:32])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:23])[CH2:16][CH2:17][CH2:18][C:19]([OH:22])([CH3:21])[CH3:20])[CH2:6]1)(=O)C.[OH-].[Na+].Cl>CO.O1CCOCC1>[OH:4][C@H:5]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C@@:7]([OH:33])([CH2:8][CH2:9][C@@H:10]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:32])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:23])[CH2:16][CH2:17][CH2:18][C:19]([OH:22])([CH3:21])[CH3:20])[CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 207395473beta-Acetoxy-5alpha,25-dihydroxy cholestane

Product 1

HCID 545286263beta, 5alpha,25-Tri-hydroxy-cholestane

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3β-acetoxy-5α,25-dihydroxy-cholestane (IV) in 40 cc of methanol and 10 cc of dioxane was treated with 6 cc of a 10% solution of sodium hydroxide and refluxed for 3 hours. The reaction mixture was neutralized with a solution of 5% aqueous hydrochloric acid, extracted with ether and washed with water. The ether solution was evaporated in vacuo and the residue was recrystallized from ether to give 850 mg of the 3β, 5α,25-tri-hydroxy-cholestane (VI) m.p. 202°-204° Nmr δ 0.67 (s, 3H), 0.9 (d, J=5 cps, 3H), 1.22 (s, 6H).

Workup

  1. temperaturerefluxed for 3 hours
  2. extractionextracted with ether
  3. washwashed with water
  4. customThe ether solution was evaporated in vacuo
  5. customthe residue was recrystallized from ether

Sources & evidence

ORD record
ord-f1df168a7ff341b6b33e359bb3ef9838
Source dataset
uspto-grants-1976_06
Patent number
US03963765

Reaction notes

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