Water → HCID 54123535, compound

HRID 1415848Notes

Reaction equation

HRID 1415848 reaction equation
[CH3:1][C:2](=[O:22])[C: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][CH2:12][CH:13]=[CH:14]2)[CH2:9][CH2:8]3)[CH2:5][CH:4]=1.[CH3:23][Al](C)C.O>O1CCOCC1.C1(C)C=CC=CC=1>[CH3:23][C@@H:4]1[CH2:5][C@@H:6]2[C@:20]([CH3:21])([CH2:19][CH2:18][C@H:17]3[C@H:7]2[CH2:8][CH2:9][C:10]2[C@:15]3([CH3:16])[CH:14]=[CH:13][CH2:12][CH:11]=2)[C@H:3]1[C:2](=[O:22])[CH3:1]

Participants

6

Reactant 3

HCID 962WaterHCID 16682925TrimethylaluminumHCID 54505817HCID 54505817, compound

Product 1

HCID 54123535HCID 54123535, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
25 °C

Procedure

3.1 g (10 mmol) of pregna-1,4,16-trien-20-one is mixed in 25 ml of dioxane with 143.4 mg of CuBr. 9.4 ml (11 mmol) of a 10% solution of trimethyl aluminum in toluene is added to the reaction under nitrogen and stirred for 30 minutes at 20-30° C. For hydrolysis, 0.54 ml of water dissolved in 5 ml of dioxane is added to the reaction. It is stirred for 10 minutes more and the precipitate is filtered off. The precipitate is washed again with a little dioxane. The dioxane solution is concentrated by evaporation on a rotary evaporator and the residue is chromatographed on silica gel with ethyl acetate/hexane as eluent. After concentration by evaporation of the fractions, 2.6 g of 16α-methyl-pregna-1,4-dien-20-one (80% of theory) of a melting point of 175° C. is obtained.

Workup

  1. additionis added to the reaction
  2. stirringIt is stirred for 10 minutes more
  3. filtrationthe precipitate is filtered off
  4. washThe precipitate is washed again with a little dioxane
  5. concentrationThe dioxane solution is concentrated by evaporation on a rotary evaporator
  6. customthe residue is chromatographed on silica gel with ethyl acetate/hexane as eluent
  7. concentrationAfter concentration
  8. customby evaporation of the fractions, 2.6 g of 16α-methyl-pregna-1,4-dien-20-one (80% of theory) of a melting point of 175° C.
  9. customis obtained

Sources & evidence

ORD record
ord-7afe92d33259454f992cbfb6982ce217
Source dataset
uspto-grants-1999_06
Patent number
US05908944

Reaction notes

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