Water → HCID 70506348, compound

HRID 2418136Notes

Reaction equation

HRID 2418136 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@:7]3([O:30][C@@H:8]3[C@@H:9](Cl)[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[C@@H:12]3[CH2:28][C@@H:13]3[C:14]32OCC[O:24]3)[CH2:6]1)(=[O:3])[CH3:2].O>O1CCCC1.C(O)(=O)C.[Zn]>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@:7]([OH:30])([CH:8]=[CH:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH:12]3[CH2:28][C@@H:13]3[C:14]2=[O:24])[CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 962WaterHCID 88717769HCID 88717769, compound

Product 1

HCID 70506348HCID 70506348, compoundYield 80.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 21 g of 3β-acetoxy-7α-chloro-5β,6β-epoxy-17,17-ethylenedioxy-15β,16β-methylene-5β-androstane in 105 ml of tetrahydrofuran, 105 ml of acetic acid, and 27 ml of water is combined with 63 g of zinc dust and stirred for 1.5 hours at 80° C. The mixture is then decanted off from the zinc, washed with methylene chloride, and the organic phase is washed with sodium bicarbonate solution and water. After drying and evaporation, the residue is chromatographed on silica gel, thus obtaining 13.8 g of 3β-acetoxy-5-hydroxy-15,16β-methylene-5β-androst-6-en-17-one, mp 191°-194° C.

Workup

  1. customThe mixture is then decanted off from the zinc
  2. washwashed with methylene chloride
  3. washthe organic phase is washed with sodium bicarbonate solution and water
  4. customAfter drying
  5. customevaporation
  6. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-ca030d45877644d4880566c0eb34a1c4
Source dataset
uspto-grants-1984_09
Patent number
US04472310

Reaction notes

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