Estrone → HCID 53662925, compound

HRID 1576350Notes

Reaction equation

HRID 1576350 reaction equation
[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.[C:21]1([CH2:27][C:28](Cl)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>N1C=CC=CC=1.O>[C:21]1([CH2:27][C:28]([O:20][C:9]2[CH:8]=[CH:7][C:6]3[C@@H:5]4[C@H:14]([C@H:15]5[C@@:2]([CH2:3][CH2:4]4)([CH3:1])[C:18](=[O:19])[CH2:17][CH2:16]5)[CH2:13][CH2:12][C:11]=3[CH:10]=2)=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 5870EstroneHCID 7679Phenylacetyl chloride

Product 1

HCID 53662925HCID 53662925, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Oestrone (2 g.) in pyridine (10 ml.) was treated for three days at room temperature with phenylacetyl chloride (3 ml.). The mixture was diluted with water (50 ml.) and the product extracted with ether (50 ml.) containing a little chloroform. The extract was washed with water (50 ml.) then 2N-sulphuric acid (25 ml.) then water again (50 ml.) and the solvent was evaporated in vacuo. Filtration of the residue in methylene chloride through a short Florisil column and crystallisation from light petroleum (b.p. 40°/60°)-ether gave the title compound in two crops (total 1.54 g., 54%), m.p. 114°-116°.

Workup

  1. extractionthe product extracted with ether (50 ml.)
  2. additioncontaining a little chloroform
  3. washThe extract was washed with water (50 ml.)
  4. custom2N-sulphuric acid (25 ml.) then water again (50 ml.) and the solvent was evaporated in vacuo
  5. filtrationFiltration of the residue in methylene chloride
  6. customthrough a short Florisil column and crystallisation from light petroleum (b.p. 40°/60°)-ether

Sources & evidence

ORD record
ord-169d2b2ef04346e5990ec84096af400e
Source dataset
uspto-grants-1976_09
Patent number
US03980681

Reaction notes

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