Methanol → HCID 15463286, compound

HRID 1953498Notes

Reaction equation

HRID 1953498 reaction equation
C=[CH:2][C@@H:3]1[C@:20]2([CH3:21])[C@H:6]([C@H:7]3[C@H:17]([CH2:18][CH2:19]2)[C@:15]2([CH3:16])[C:10](=[CH:11][C:12](=[O:22])[CH2:13][CH2:14]2)[C:9](=O)[CH2:8]3)[CH2:5][CH2:4]1.[CH3:24]OC(OC)(C)C.CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C=O)C>[CH3:24][O:22][C:12]1[CH2:13][CH2:14][C@@:15]2([CH3:16])[C:10](=[CH:9][CH2:8][C@@H:7]3[C@@H:17]2[CH2:18][CH2:19][C@@:20]2([CH3:21])[C@H:6]3[CH2:5][CH2:4][C:3]2=[CH2:2])[CH:11]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 15429665Pregna-4,20-dien-3,6-dione

Product 1

HCID 15463286HCID 15463286, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Refer to FIG. 190. To 17-methylenandrost-4-en-3-one (9, 2.0000 g, 7.0314 mmol) in 2,2-dimethoxypropane (9.4 ml, 76 mmol) and DMF (9.4 ml) were added 0.37 ml of anh. methanol and 47.0 mg of p-toluenesulfonic acid. After refluxing 4 h the reaction mixture was allowed to cool and then partitioned between 140 ml of hexanes and 90 ml of water. The organic phase was washed with two 90 ml portions of water+90 ml of brine, dried over magnesium sulfate, and flash filtered through a 30 mm dia.×37 mm high column of silica gel (200-400 mesh). Product continued eluting with 200 ml of hexanes. Concentration of the combined filtrates under reduced pressure and recrystallization of the residue from acetone/methanol gave very slightly yellow platelets (1.5291 g, 5.1231 mmol, 73%), m.p. 97-99° C., homogeneous to TLC (25% ethyl acetate/hexanes on silica gel, Rf 0.72).

Workup

  1. temperatureAfter refluxing 4 h the reaction mixture
  2. temperatureto cool
  3. custompartitioned between 140 ml of hexanes and 90 ml of water
  4. washThe organic phase was washed with two 90 ml portions of water+90 ml of brine
  5. dry with materialdried over magnesium sulfate, and flash
  6. filtrationfiltered through a 30 mm dia
  7. washProduct continued eluting with 200 ml of hexanes
  8. customConcentration of the combined filtrates under reduced pressure and recrystallization of the residue from acetone/methanol
  9. customgave very slightly yellow platelets (1.5291 g, 5.1231 mmol, 73%), m.p. 97-99° C.

Sources & evidence

ORD record
ord-a1e4259a85e54d0b838fbc9213a2c2c1
Source dataset
uspto-grants-2000_09
Patent number
US06117860

Reaction notes

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