Dimethylformamide → 16beta-Ethyl-17beta-n-heptanoyloxyacetoxy-4-estren-3-one

HRID 64727

Reaction equation

HRID 64727 reaction equation
[C:1]([OH:9])(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[OH-].[Na+].[CH2:12]([C@H:14]1[CH2:19][C@H:18]2[C@H:20]3[C@H:29]([CH2:30][CH2:31][C@:16]2([CH3:17])[C@H:15]1[O:33][C:34](=[O:37])[CH2:35]Br)[C@@H:28]1[C:23](=[CH:24][C:25](=[O:32])[CH2:26][CH2:27]1)[CH2:22][CH2:21]3)[CH3:13].CN(C=O)C>CC(C)=O.C(OCC)(=O)C.O>[CH2:12]([C@H:14]1[CH2:19][C@H:18]2[C@H:20]3[C@H:29]([CH2:30][CH2:31][C@:16]2([CH3:17])[C@H:15]1[O:33][C:34](=[O:37])[CH2:35][O:8][C:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[C@@H:28]1[C:23](=[CH:24][C:25](=[O:32])[CH2:26][CH2:27]1)[CH2:22][CH2:21]3)[CH3:13]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8094Heptanoic AcidHCID 14798Sodium HydroxideHCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one

Product 1

HCID 7046764616beta-Ethyl-17beta-n-heptanoyloxyacetoxy-4-estren-3-oneYield 64%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 30 ml of acetone is dissolved 2.6 g of n-heptanoic acid, and 10 ml of 2N-NaOH, 4.2 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one, 30 ml of DMF and 10 ml of water are serially added to the above solution. The mixture is refluxed for 5 hours. After cooling, 400 ml of ethyl acetate is added and the mixture is washed with water and saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is subjected to column chromatography. Following 400 ml of diisopropyl ether-n-hexane (2:3), elution is carried out with 1000 ml of a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 3.0 g of the above-identified compound as a light-yellow viscous oil.

Workup

  1. additionare serially added to the above solution
  2. temperatureThe mixture is refluxed for 5 hours
  3. temperatureAfter cooling
  4. washthe mixture is washed with water and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent is then distilled off under reduced pressure
  7. wash400 ml of diisopropyl ether-n-hexane (2:3), elution
  8. additionis carried out with 1000 ml of a 1:1 mixture of the same solvents
  9. customThe eluate is evaporated under reduced pressure
  10. customto remove the solvent

Sources & evidence

ORD record
ord-51711f58cf9043d294756a7ccce7d9b7
Source dataset
uspto-grants-1986_09
Patent number
US04609650

Linked notes

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