Estrone → 975-64-4

HRID 1576354Notes

Reaction equation

HRID 1576354 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:20])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1>N1C=CC=CC=1.C(OC(=O)CC)(=O)CC>[C:2]([O:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:20])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1)(=[O:1])[CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 5870Estrone

Product 1

HCID 54277166975-64-4Yield 173.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 31263Propionic anhydrideSolvent

Procedure

3-Hydroxy-oestra-1,3,5(10)-trien-17-one (2 g) in pyridine (20 ml.) and propionic anhydride (20 ml) was allowed to stand at room temperature for 1 hour. The solution was poured into ice-water (250 ml) and the precipitated steroid was extracted into ethyl acetate. The organic solution was washed with sodium carbonate solution, then water, dried and the solvent was evaporated. Crystallisation from ethyl acetate gave the title compound (2.10 g, 88%). m.p. 134°-6°, [α]D + 136° (c. 1.03).

Workup

  1. extractionthe precipitated steroid was extracted into ethyl acetate
  2. washThe organic solution was washed with sodium carbonate solution
  3. dry with materialwater, dried
  4. customthe solvent was evaporated
  5. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-ace9d667523e40b088091efa6d40fd0b
Source dataset
uspto-grants-1976_09
Patent number
US03980681

Reaction notes

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