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Ethyl Acetate → 16beta-Ethyl-17beta-n-hexanoyloxyacetoxy-4,9(10)-estradien-3-one

HRID 64734
Notes
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Reaction equation

HRID 64734 reaction equation
[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[OH:22])=[C:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2].[C:23]([O:30][CH2:31][C:32](Cl)=[O:33])(=[O:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[O:22][C:32](=[O:33])[CH2:31][O:30][C:23](=[O:29])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[C:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 12831651HCID 12831651, compoundHCID 147665592-Chloro-2-oxoethyl hexanoate

Product 1

HCID 1860425916beta-Ethyl-17beta-n-hexanoyloxyacetoxy-4,9(10)-estradien-3-one

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

In 20 ml of toluene are dissolved 1.5 g of 16β-ethyl-17β-hydroxy-4,9(10)-estradien-3-one and 1.92 g of 4-dimethylaminopyridine, and 1.6 ml of n-hexanoyloxyacetyl chloride is added. The mixture is stirred at 50°-60° C. for 3 hours. After cooling to 25° C., the mixture is poured into a mixture of ethyl acetate (200 ml) and saturated aqueous sodium hydrogen carbonate (50 ml). The organic layer is separated and the aqueous layer is extracted with ethyl acetate. These organic layers are combined, 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 chromatographed on a silica gel column. Following passage of diisopropyl ether-n-hexane (1:1), elution is carried out with 1000 ml of a 3:2 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.69 g of the above-identified compound as a light-yellow viscous oil.

Workup

  1. additionis added
  2. customThe organic layer is separated
  3. extractionthe aqueous layer is extracted with ethyl acetate
  4. washwashed 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. customthe residue is chromatographed on a silica gel column
  8. washpassage of diisopropyl ether-n-hexane (1:1), elution
  9. additionis carried out with 1000 ml of a 3:2 mixture of the same solvents
  10. customThe eluate is evaporated under reduced pressure
  11. customto remove the solvent

Sources & evidence

ORD record
ord-38de621d11e3468f857ce3b881a9a486
Source dataset
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04609650

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes