HCID 10852787, compound → HCID 15429666, compound

HRID 1107191Notes

Reaction equation

HRID 1107191 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[CH3:14][C:15]([C@@H:17]1[C@:34]2([CH3:35])[C@H:20]([C@H:21]3[C@H:31]([CH2:32][CH2:33]2)[C@:29]2([CH3:30])[C:24]([CH2:25][C@@H:26]([OH:36])[CH2:27][CH2:28]2)=[CH:23][CH2:22]3)[CH2:19][CH2:18]1)=[CH2:16]>CC(C)=O>[CH3:16][C:15]([C@@H:17]1[C@:34]2([CH3:35])[C@H:20]([C@H:21]3[C@H:31]([CH2:32][CH2:33]2)[C@:29]2([CH3:30])[C:24](=[CH:25][C:26](=[O:36])[CH2:27][CH2:28]2)[C:23](=[O:3])[CH2:22]3)[CH2:19][CH2:18]1)=[CH2:14]

Participants

4

Reactant 2

HCID 10852787HCID 10852787, compoundHCID 131709961Jones' reagent

Product 1

HCID 15429666HCID 15429666, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones reagent (2.67 M, 1.83 ml, 4.89 mmol) was added to a solution of 20-methylpregna-5,20-dien-3β-ol (400.0 mg, 1.272 mmol) in 45 ml of acetone and the reaction was stirred 20 min. After quenching with 2-propanol (0.91 ml) the mixture was poured into 85 ml of water and extracted three times with 40 ml portions of ethyl acetate. The combined organic extracts were washed with 40 ml of saturated sodium bicarbonate+40 ml of brine, dried over magnesium sulfate, and filtered through diatomaceous earth. The residue was washed with 25 ml of ethyl acetate and the combined filtrates were concentrated under reduced pressure. Recrystallization of the solid residue from aqueous ethanol gave yellow crystals (235.0 mg, 0.7298 mmol, 57%), m.p. 148-150° C. TLC (20% ethyl acetate/hexanes on silica gel) showed a major product at Rf 0.24 with a minor impurity at the origin.

Workup

  1. customAfter quenching with 2-propanol (0.91 ml) the mixture
  2. additionwas poured into 85 ml of water
  3. extractionextracted three times with 40 ml portions of ethyl acetate
  4. washThe combined organic extracts were washed with 40 ml of saturated sodium bicarbonate+40 ml of brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered through diatomaceous earth
  7. washThe residue was washed with 25 ml of ethyl acetate
  8. concentrationthe combined filtrates were concentrated under reduced pressure
  9. customRecrystallization of the solid residue from aqueous ethanol

Sources & evidence

ORD record
ord-c0a6df4772eb4a7e8a118a515813664d
Source dataset
uspto-grants-2000_05
Patent number
US06057439

Reaction notes

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