1,4-Dioxane → HCID 86751848, compound

HRID 725183Notes

Reaction equation

HRID 725183 reaction equation
[OH:1][CH2:2]/[CH:3]=[CH:4]/[C@@H:5]1[C@:13]2([CH3:14])[C@@:8]([OH:29])([CH2:9][C@@H:10]([C:15]3[CH:20]=[C:19](C)[C:18](C(C)(C)C)=[C:17](C)[C:16]=3O[SiH3])[CH2:11][CH2:12]2)[CH2:7][CH2:6]1.[O:30]1CCOCC1>O=[Mn]=O>[CH:2](/[CH:3]=[CH:4]/[C@@H:5]1[C@:13]2([CH3:14])[C@@:8]([OH:29])([CH2:9][C@@H:10]([C:15]3[CH:20]=[CH:19][C:18]([OH:30])=[CH:17][CH:16]=3)[CH2:11][CH2:12]2)[CH2:7][CH2:6]1)=[O:1]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 131720378HCID 131720378, compound

Product 1

HCID 86751848HCID 86751848, compound

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Procedure

To a solution of 2.90 g of (1R,3aS,5S,7aR)-1-[(E)-3-hydroxy-1-propenyl]-5-(4-tert-butyldimethyl-silyloxyphenyl)-7a-methylperhydroinden-3a-ol in 40 ml of dioxane, 13.80 g of MnO2 were added while cooling in an ice bath. The mixture was stirred at room temperature for 1 hr, filtered through celite and the filtrate was made acid to pH 1 with 3N HCl and, using the same procedure described in Prepn, 1, the title compound (II-bb) (2.75 g) was obtained as a white solid.

Workup

  1. temperaturewhile cooling in an ice bath
  2. filtrationfiltered through celite

Sources & evidence

ORD record
ord-d3eb7d36cf924c908a070994f921dbb4
Source dataset
uspto-grants-1998_01
Patent number
US05705531

Reaction notes

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