Methanol → 3-Keto-5alpha,25-dihydroxy-cholestane

HRID 1658419Notes

Reaction equation

HRID 1658419 reaction equation
[OH:1][C@H:2]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@@:4]([OH:30])([CH2:5][CH2:6][C@@H:7]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:29])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:20])[CH2:13][CH2:14][CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[CH2:3]1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.CO>CC(C)=O>[O:1]=[C:2]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@@:4]([OH:30])([CH2:5][CH2:6][C@@H:7]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:29])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:20])[CH2:13][CH2:14][CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 545286263beta, 5alpha,25-Tri-hydroxy-cholestaneHCID 131709961Jones' reagent

Product 1

HCID 207395503-Keto-5alpha,25-dihydroxy-cholestaneYield 76.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 750 mg of the 3β ,5α -25-trihydroxy-cholestane (VI) in 300 ml of acetone was treated dropwise with 10cc of Jones reagent. The reaction mixture was treated with 10 ml of methanol, left for 15 minutes at room temperature and concentrated in vacuum. The residue was extracted with ether and washed with water. The ether extract was evaporated in vacuo and the residue was crystallized from benzene to give 570 mg of 3-keto-5α,25-dihydroxy-cholestane (VII) m.p. 215°-217°. Nmr δ 0.70 (s, 3H), 1.15 (s, 3H), 0.95 (d, J=5Hz, 1H), 1.22 (s, 3H) Anal. Calcd for C27H46O2 : C, 77.5; H, 11.1%. Found: C, 77.0; H, 10.5%.

Workup

  1. concentrationconcentrated in vacuum
  2. extractionThe residue was extracted with ether
  3. washwashed with water
  4. extractionThe ether extract
  5. customwas evaporated in vacuo
  6. customthe residue was crystallized from benzene

Sources & evidence

ORD record
ord-021cde6579204277976e3b3c02ffbd91
Source dataset
uspto-grants-1976_06
Patent number
US03963765

Reaction notes

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