2,2-Dimethoxypropane → HCID 67362263, compound

HRID 2413539Notes

Reaction equation

HRID 2413539 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:11]2[C@H:12]3[C@H:21]([CH2:22][CH2:23][C@:8]2([CH2:9][CH3:10])[C:7](=[O:25])[CH2:6]1)[C@@H:20]1[C:15](=[CH:16][C:17](=[O:24])[CH2:18][CH2:19]1)[CH2:14][CH2:13]3)(=[O:3])[CH3:2].[CH3:26]OC(OC)(C)C.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>CN(C)C=O.CO>[C:1]([O:4][C@@H:5]1[C@H:11]2[C@H:12]3[C@H:21]([CH2:22][CH2:23][C@:8]2([CH2:9][CH3:10])[C:7](=[O:25])[CH2:6]1)[C@@H:20]1[C:15]([CH:16]=[C:17]([O:24][CH3:26])[CH2:18][CH2:19]1)=[CH:14][CH2:13]3)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 64952,2-DimethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 67361589HCID 67361589, compound

Product 1

HCID 67362263HCID 67362263, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

60.0 g of 15α-acetoxy-18-methyl-4-estrene-3,17-dione in 500 ml of dimethylformamide is stirred with 500 ml of 2,2-dimethoxypropane, 20 ml of methanol and 6.0 g of pyridinium tosylate at 110° C. under argon. After 3.5 hours, 9.0 g of solid sodium bicarbonate is added, the reaction mixture is stirred into 10 liters of ice/water, the precipitated product is suctioned off, washed repeatedly with water, and dried under vacuum at 70° C. The crude product is suspended in 375 ml of methanol and stirred under reflux for 15 minutes. After gradual cooling down to room temperature, the colorless crystallized product is suctioned off and washed with cold methanol. Yield: 56 g of 15α-acetoxy-3-methoxy-18-methyl-3,5-estradien-17-one. Melting point 190° C.

Workup

  1. washwashed repeatedly with water
  2. customdried under vacuum at 70° C
  3. temperatureunder reflux for 15 minutes
  4. washwashed with cold methanol

Sources & evidence

ORD record
ord-82b5d43b927c45ad8ab13ef275de31ce
Source dataset
uspto-grants-1988_01
Patent number
US04719054

Reaction notes

Loading…