Acetic Anhydride → HCID 54283311, compound

HRID 1414969Notes

Reaction equation

HRID 1414969 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C:9]3[C:12]4[CH:13]=[CH:14][C:15]([OH:20])=[CH:16][C:17]=4[CH2:18][CH2:19][C:8]=3[C:7]1=[CH:6][CH2:5][C:4]2=[O:21])[CH3:2].[C:22](OC(=O)C)(=[O:24])[CH3:23]>N1C=CC=CC=1>[CH2:1]([C@:3]12[CH2:11][CH2:10][C:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:20][C:22](=[O:24])[CH3:23])=[CH:16][C:17]=4[CH2:18][CH2:19][C:8]=3[C:7]1=[CH:6][CH2:5][C:4]2=[O:21])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54013930HCID 54013930, compound

Product 1

HCID 54283311HCID 54283311, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Dissolve 13β-ethyl-3-hydroxygona-1,3,5(10),8,14-pentaen-17-one (2.45 g) in pyridine (7 cc) and acetic anhydride (4 cc) and allow to stand at room temperature for 16 hours. Remove the solvent under reduced pressure, add ethanol (20 cc) and again evaporate the solvent. Recrystallize the residue from ethanol to give a red crystalline solid, m.p. 122°-124°. Filter the solid through `Florisil` (100 g) with benzene, evaporate the solvent and recrystallize the product from ethanol to obtain 13β-ethyl-3-acetoxygona-1,3,5(10),8,14-pentaen-17-one, m.p. 129°-130°C; ultraviolet absorption peak at 306 mμ (ε25,500), infrared absorption peaks at 5.78 μ, 8.27 μ, and 9.85 μ.

Workup

  1. customRemove the solvent under reduced pressure
  2. additionadd ethanol (20 cc)
  3. customagain evaporate the solvent
  4. customRecrystallize the residue from ethanol
  5. customto give a red crystalline solid, m.p. 122°-124°
  6. filtrationFilter the solid through `Florisil` (100 g) with benzene
  7. customevaporate the solvent
  8. customrecrystallize the product from ethanol

Sources & evidence

ORD record
ord-ce2f1cbb40a8404092c250046ddb1885
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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