Water → HCID 86736881, compound

HRID 1701455Notes

Reaction equation

HRID 1701455 reaction equation
ClCC([O:5][C@H:6]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@@H:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:22]2[C@@H:21]([O:27][C:28](=[O:31])[CH2:29][Cl:30])[CH2:20][C@@:19]2([CH3:32])[C@H:12]3[CH2:13][CH:14]=[C:15]2[C:16](=[O:18])[CH3:17])[CH2:7]1)=O.O.C(=O)(O)[O-].[Na+]>O1CCOCC1>[Cl:30][CH2:29][C:28]([O:27][C@H:21]1[CH2:20][C@@:19]2([CH3:32])[C@@H:12]([CH2:13][CH:14]=[C:15]2[C:16](=[O:18])[CH3:17])[C@H:11]2[C@H:22]1[C@:23]1([CH3:26])[C@@H:8]([CH2:9][CH2:10]2)[CH2:7][C@@H:6]([OH:5])[CH2:25][CH2:24]1)=[O:31]

Participants

5

Reactant 3

HCID 962Water2×HCID 516892Sodium BicarbonateHCID 86736882HCID 86736882, compound

Product 1

HCID 86736881HCID 86736881, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3β,11β-Bischloroacetoxy-5α-pregn-16-en-20-one (1.2 g) was stirred at 100° in dioxan (20 ml) containing water (4 ml) with sodium bicarbonate (1.26 g) for 4 hours. The mixture was cooled, poured into water and the precipitate collected by filtration, dried and filtered through silica gel (20 g) in ethylacetate. The eluate was evaporated and the residue crystallised from petrol containing a little ethyl acetate to yield the title compound (684 mg), m.p. 160.5°-162°, [α]D +75.2°.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe precipitate collected by filtration
  3. customdried
  4. filtrationfiltered through silica gel (20 g) in ethylacetate
  5. customThe eluate was evaporated
  6. customthe residue crystallised from petrol containing a little ethyl acetate

Sources & evidence

ORD record
ord-ef3eea05b035461ea020951a41d570b0
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

Loading…