Pyridine → HCID 22820399, compound

HRID 1156042Notes

Reaction equation

HRID 1156042 reaction equation
[OH:1][C@H:2]1[C@H:7]([CH3:8])[CH2:6][C@H:5]2[C@H:9]3[C:18]([CH2:19][CH2:20][C@:3]12[CH3:4])=[C:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3.[C:22]([O-:25])(O)=O.[Na+].N1C=CC=C[CH:28]=1>C(OC(=O)C)(=O)C>[C:22]([O:1][C@H:2]1[C@H:7]([CH3:8])[CH2:6][C@H:5]2[C@H:9]3[C:18]([CH2:19][CH2:20][C@:3]12[CH3:4])=[C:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)(=[O:25])[CH3:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 22820402HCID 22820402, compound

Product 1

HCID 22820399HCID 22820399, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 7.8 g of 17β-hydroxy-16α-methyl-4,9(10)-estradien-3-one in 25 ml of pyridine and 8 ml of acetic anhydride is stirred for 6 hours at 50° C. under argon. After cooling the mixture is poured into saturated NaHCO3 solution and extracted with ethyl acetate. The ethyl acetate extracts are washed in succession with water, 2 N hydrochloric acid, and saturated NaCl solution, dried over sodium sulfate, and concentrated. Crystallization from ether yields 6.6 g of 17β-acetoxy-16α-methyl-4,9(10)-estradien-3-one, m.p. 124°-126° C.

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate extracts are washed in succession with water, 2 N hydrochloric acid, and saturated NaCl solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customCrystallization from ether

Sources & evidence

ORD record
ord-5bd2dc93a6f04c179b51f27da75504bd
Source dataset
uspto-grants-1982_06
Patent number
US04333928

Reaction notes

Loading…