Peracetic Acid → 3beta-Acetoxy-5alpha,25-dihydroxy cholestane

HRID 1658417Notes

Reaction equation

HRID 1658417 reaction equation
[C:1]([O:4][C@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@@:7]([OH:32])([CH2:8][CH2:9][C@@H:10]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:31])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:6]1)(=[O:3])[CH3:2].C(OCC)(=[O:35])C.C(OO)(=O)C>C(O)(=O)C>[C:1]([O:4][C@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@@:7]([OH:32])([CH2:8][CH2:9][C@@H:10]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:31])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][CH2:18][C:19]([OH:35])([CH3:21])[CH3:20])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6585Peracetic AcidHCID 8857Ethyl AcetateHCID 133406063betaAcetoxy-5alphahydroxycholestane

Product 1

HCID 207395473beta-Acetoxy-5alpha,25-dihydroxy cholestane

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 50 g 3β-acetoxy-5-α-hydroxy-cholestane (II), in 25 ml. of ethyl acetate was treated with 100 ml. of peracetic acid (70%) in acetic acid and was irradiated with ultra-violet light of about 300 mμ wavelength for 12 hours. The resulting reaction mixture was washed with a solution of aqueous sodium bisulfite, sodium bicarbonate and then with water. After evaporation of the solvent in vacuo, the residue was chromatographed on a column of silica gel to give 10 g of the novel 3β-acetoxy-5α,25-dihydroxy cholestane (IV) which was recrystallized from methanol, m.p. 180°-182°C.

Workup

  1. customThe resulting reaction mixture
  2. washwas washed with a solution of aqueous sodium bisulfite, sodium bicarbonate
  3. customAfter evaporation of the solvent in vacuo
  4. customthe residue was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-c3a49ba7f43741a684fb0efe80af4ee6
Source dataset
uspto-grants-1976_06
Patent number
US03963765

Reaction notes

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