Water → HCID 70363058, compound

HRID 1650787Notes

Reaction equation

HRID 1650787 reaction equation
[CH2:1]([CH:3]1[C@H:8]2[C@H:9]3[C@H:20]([CH2:21][CH2:22][C@:6]2([CH3:7])[C:5](=[O:24])[CH2:4]1)[C@:17]1([CH2:18][OH:19])[C:12](=[CH:13][C:14](=O)[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2].[CH2:25]([Li])CCC.O>O1CCCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([CH:3]1[C@H:8]2[C@H:9]3[C@H:20]([CH2:21][CH2:22][C@:6]2([CH3:7])[C:5](=[O:24])[CH2:4]1)[C@:17]1([CH2:18][OH:19])[C:12](=[CH:13][C:14](=[CH2:25])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 70362947HCID 70362947, compoundHCID 178418339Butyllithium

Product 1

HCID 70363058HCID 70363058, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

2.7 g of 15-alpha-ethyl-19-hydroxy-4-androstene-3,17-dione in 25 ml of tetrahydrofuran is instilled in a suspension of 28.6 of methyl triphenylphosphonium bromide in 200 ml of tetrahydrofuran, which was stirred with 200 ml of butyllithium solution (1.6 m in ether) for 1.5 hours at 20° C., and stirred for one hour at 20° C. Then it is mixed with water, extracted three times with ethyl acetate, washed neutral, dried on sodium sulfate and is freed from the solvent in a vacuum. After chromatographic purification on silica gel with hexane/ethyl acetate, 1.95 g of pure 15-alpha-ethyl-3-methylene-19-hydroxy-4-androsten-17-one is obtained as foam.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washwashed neutral
  3. customdried on sodium sulfate
  4. customAfter chromatographic purification on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-808429316cc84d1ea2fc1694f4aaf715
Source dataset
uspto-grants-1990_05
Patent number
US04925834

Reaction notes

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