HCID 57236229, compound → HCID 53668100, compound

HRID 2270513Notes

Reaction equation

HRID 2270513 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[CH3:14][C:15]([C@@H:18]1[C@:35]2([CH3:36])[C@H:21]([C@H:22]3[C@H:32]([CH2:33][CH2:34]2)[C@:30]2([CH3:31])[C:25]([CH2:26][C@@H:27]([OH:37])[CH2:28][CH2:29]2)=[CH:24][CH2:23]3)[CH2:20][CH2:19]1)=[CH:16][CH3:17]>CC(C)=O>[CH3:14][C:15]([C@@H:18]1[C@:35]2([CH3:36])[C@H:21]([C@H:22]3[C@H:32]([CH2:33][CH2:34]2)[C@:30]2([CH3:31])[C:25](=[CH:26][C:27](=[O:37])[CH2:28][CH2:29]2)[C:24](=[O:3])[CH2:23]3)[CH2:20][CH2:19]1)=[CH:16][CH3:17]

Participants

4

Reactant 2

HCID 57236229HCID 57236229, compoundHCID 131709961Jones' reagent

Product 1

HCID 53668100HCID 53668100, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones reagent (2.67M, 2.0 ml. 5.3 mmol) was added to a solution of 20,21 -dimethylpregna-5,20-dien-3β-ol (6, 460.1 mg, 1.400 mmol) in 50 ml of acetone and the reaction was stirred 45 min. After quenching with 2-propanol (1.0 ml) the mixture was poured into 100 ml of water and extracted three times with 50 ml of ethyl acetate. The combined organic extracts were washed with 50 ml of saturated sodium bicarbonate+50 ml of brine, dried over magnesium sulfate, and filtered through Celite. The residue was washed with 25 ml of ethyl acetate and the combined filtrates were concentrated under reduced pressure. Flash chromatography (25% ethyl acetate/hexanes on silica gel) and recrystallization of the residue from 95% ethanol gave yellow needles (138.2 mg, 0.4059 mmol, 29%), m.p. 172-178° C.

Workup

  1. customAfter quenching with 2-propanol (1.0 ml) the mixture
  2. additionwas poured into 100 ml of water
  3. extractionextracted three times with 50 ml of ethyl acetate
  4. washThe combined organic extracts were washed with 50 ml of saturated sodium bicarbonate+50 ml of brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered through Celite
  7. washThe residue was washed with 25 ml of ethyl acetate
  8. concentrationthe combined filtrates were concentrated under reduced pressure
  9. customFlash chromatography (25% ethyl acetate/hexanes on silica gel) and recrystallization of the residue from 95% ethanol

Sources & evidence

ORD record
ord-f4eebea191b44434a73893e8243c48c0
Source dataset
uspto-grants-2001_12
Patent number
US06331534B1

Reaction notes

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