Ethyl Acetate → HCID 70467844, compound

HRID 64718Notes

Reaction equation

HRID 64718 reaction equation
[OH:1][CH:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4].[OH-].[Na+].[CH2:10]([C@H:12]1[CH2:17][C@H:16]2[C@H:18]3[C@H:27]([CH2:28][CH2:29][C@:14]2([CH3:15])[C@H:13]1[O:31][C:32](=[O:35])[CH2:33]Br)[C@@H:26]1[C:21](=[CH:22][C:23](=[O:30])[CH2:24][CH2:25]1)[CH2:20][CH2:19]3)[CH3:11].C(OCC)(=O)C>CN(C=O)C>[CH2:10]([C@H:12]1[CH2:17][C@H:16]2[C@H:18]3[C@H:27]([CH2:28][CH2:29][C@:14]2([CH3:15])[C@H:13]1[O:31][C:32](=[O:35])[CH2:33][O:4][C:3](=[O:5])[CH:2]([OH:1])[CH2:6][CH3:7])[C@@H:26]1[C:21](=[CH:22][C:23](=[O:30])[CH2:24][CH2:25]1)[CH2:20][CH2:19]3)[CH3:11]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 112662-Hydroxybutyric AcidHCID 14798Sodium HydroxideHCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one

Product 1

HCID 70467844HCID 70467844, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 40 ml of DMF is dissolved 0.6 g of α-hydroxybutyric acid, and 6.0 ml of 1N-NaOH and 1.4 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one are added. The mixture is stirred at room temperature (15°-25° C.) for 16 hours. To the reaction mixture is added 150 ml of ethyl acetate and the mixture is washed with water and saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent is then distilled off under reduced pressure and the residue is subjected to column chromatography. Following passage of 50 ml of dichloromethane and 100 ml of diisopropyl ether in that order, elution is carried out with 150 ml of diisopropyl ether and 250 ml of diisopropyl ether-ethyl acetate (1:10). The eluates are combined and evaporated under reduced pressure to remove the solvent, giving 0.82 g of the above-identified compound as a colorless viscous oil.

Workup

  1. additionare added
  2. washthe mixture is washed with water and saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent is then distilled off under reduced pressure
  5. washin that order, elution
  6. customevaporated under reduced pressure
  7. customto remove the solvent

Sources & evidence

ORD record
ord-62ad87b090ba4a03aca5d7c5fddf5314
Source dataset
uspto-grants-1986_09
Patent number
US04609650

Reaction notes

Loading…