Water → HCID 15432774, compound

HRID 1935986Notes

Reaction equation

HRID 1935986 reaction equation
[OH:1][C@H:2]1[CH2:7][C@@H:6]2[CH2:8][C@:5]32[C@H:9]2[C@H:18]([CH2:19][CH2:20][C@:3]13[CH3:4])[C@@H:17]1[C:12]([CH2:13][C:14](=[O:21])[CH2:15][CH2:16]1)=[CH:11][CH2:10]2.C(=O)(O)[O-].[Na+].O>CC(C)=O.Cl>[OH:1][C@H:2]1[CH2:7][C@@H:6]2[CH2:8][C@:5]32[C@H:9]2[C@H:18]([CH2:19][CH2:20][C@:3]13[CH3:4])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]2

Participants

6

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 15432773HCID 15432773, compound

Product 1

HCID 15432774HCID 15432774, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution that consists of 2 g of 17β-hydroxy-14α,15α-methylenestr-5-en-3-one in 95 ml of acetone and 5 ml of 5% aqueous hydrochloric acid is stirred for 2.5 hours at room temperature. Then, 10 ml of saturated aqueous sodium bicarbonate solution and 200 ml of water are added in succession. This solution is concentrated by evaporation in a vacuum rotary evaporator, whereby crystallization is used. The crystals are filtered off, dried, dissolved in acetone and applied to a silica gel column (0.063-0.2 mm, Merck). Chromatography with cyclohexane ethyl acetate 7:3 (v/v) as an eluant yields 17β-hydroxy-14α,15α-methylenestr-4-en-3-one.

Workup

  1. concentrationThis solution is concentrated by evaporation in a vacuum rotary evaporator, whereby crystallization
  2. filtrationThe crystals are filtered off
  3. customdried
  4. dissolutiondissolved in acetone

Sources & evidence

ORD record
ord-f01d343ed274447688fd02f1b1407e76
Source dataset
uspto-grants-2002_05
Patent number
US06388109B1

Reaction notes

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