Sodium Acetate → (7-alpha)-3-Methoxy-7-propylestra-1,3,5(10)-trien-17-one

HRID 1421556Notes

Reaction equation

HRID 1421556 reaction equation
C([O:4][CH:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C:19]1[CH:18]=[CH:17][C:16]([O:23][CH3:24])=[CH:15][C:14]=1[CH2:13][CH:12]3[CH2:25][CH2:26][CH3:27])(=O)C.C([O-])(=O)C.[Na+].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:24][O:23][C:16]1[CH:17]=[CH:18][C:19]2[C@@H:20]3[C@H:11]([C@H:8]4[C@@:6]([CH2:22][CH2:21]3)([CH3:7])[C:5](=[O:4])[CH2:10][CH2:9]4)[C@H:12]([CH2:25][CH2:26][CH3:27])[CH2:13][C:14]=2[CH:15]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 867554683-Methoxy-7-propylestra-1,3,5(10)-trien-17-ol acetateHCID 178418287HCID 178418287, compound

Product 1

HCID 15380114(7-alpha)-3-Methoxy-7-propylestra-1,3,5(10)-trien-17-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 10.4 g of 3-O-methyl, 7α-propylestradiol 4 in 50 ml of methylene chloride were subsequently added 15 g. of powdered sodium acetate, 30 g of silicagel and 32 g of pyridinium chlorochromate. After stirring for 1 hr the oxidation was complete. Excess reagent was destroyed by addition of 1 ml of isopropanol, followed by 150 ml of hexane 10 min. later. All the precipitates were filtered over Celite, and the filtrate was concentrated to dryness. This provided 9.6 g of essentially pure ketone 5; Rf 0.54 (hept./ethyl acetate 7/3).

Workup

  1. customExcess reagent was destroyed by addition of 1 ml of isopropanol
  2. customfollowed by 150 ml of hexane 10 min.
  3. filtrationAll the precipitates were filtered over Celite
  4. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-a4f00aabce384ad695133d1cafb513a0
Source dataset
uspto-grants-2000_06
Patent number
US06077873

Reaction notes

Loading…