Potassium Formate → 16beta-Ethyl-17beta-glycoloyloxy-4-estren-3-one

HRID 64704Notes

Reaction equation

HRID 64704 reaction equation
[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[O:22][C:23](=[O:26])[CH2:24]Br)[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2].C([O-])=[O:28].[K+]>CO>[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[O:22][C:23](=[O:26])[CH2:24][OH:28])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2]

Participants

4

Reactant 2

HCID 2735122Potassium FormateHCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one

Product 1

HCID 7046644116beta-Ethyl-17beta-glycoloyloxy-4-estren-3-oneYield 75.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5.0 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 5.0 g of potassium formate is refluxed in 100 ml of methanol for 4 hours. The solvent is distilled off under reduced pressure and water is added to the residue. The mixture is extracted with 150 ml of ethyl acetate, and the ethyl acetate layer 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 resulting crystalline precipitate is recrystallized from diethyl ether-n-hexane (1:2) to give 3.2 g of the above-identified compound as colorless crystals.

Workup

  1. distillationThe solvent is distilled off under reduced pressure and water
  2. additionis added to the residue
  3. extractionThe mixture is extracted with 150 ml of ethyl acetate
  4. washthe ethyl acetate layer 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. customthe resulting crystalline precipitate is recrystallized from diethyl ether-n-hexane (1:2)

Sources & evidence

ORD record
ord-b6af3c6a671240c1b9147dbf61ec04fa
Source dataset
uspto-grants-1986_09
Patent number
US04609650

Reaction notes

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