Water → Pregna-4,20-dien-3,6-dione

HRID 2270515Notes

Reaction equation

HRID 2270515 reaction equation
[CH2:1]=[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]([CH2:11][C@@H:12]([OH:22])[CH2:13][CH2:14]2)=[CH:9][CH2:8]3)[CH2:5][CH2:4]1.CC(C)=[O:25].OS(O)(=O)=O.O=[Cr](=O)=O.CC(O)C.O>CC(C)=O>[CH2:1]=[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:25])[CH2:8]3)[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 14263442PregnadienolHCID 131709961Jones' reagent2×

Product 1

HCID 15429665Pregna-4,20-dien-3,6-dione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of pregna-5,20-dien-3β-ol (300.5 mg, 1.000 mmol) in 35 ml of acetone was cooled in an ice water bath and 2.67M Jones reagent (0.71 ml, 1.9 mmol) was added. After stirring 1½ h a further 0.71 ml of Jones reagent were added and the reaction was continued 45 min, 2-Propanol (1.0 ml) was added and the mixture was poured into 100 ml of water. The mixture was then extracted twice with 50 ml of ethyl acetate and the combined organic extracts were washed with 50 ml of saturated sodium bicarbonate+50 ml of water+50 ml of brine and filtered through a 21 mm dia×22 mm high column of silica gel 60. The column was eluted further with 25 ml of ethyl acetate and the combined filtrates were concentrated under reduced pressure. Recrystallization of the residue from 95% ethanol gave a light yellow powder (104.6 mg, 0.3348 mmol 33%), m.p. 114-120° C.

Workup

  1. additionwere added
  2. extractionThe mixture was then extracted twice with 50 ml of ethyl acetate
  3. washthe combined organic extracts were washed with 50 ml of saturated sodium bicarbonate+50 ml of water+50 ml of brine
  4. filtrationfiltered through a 21 mm
  5. washThe column was eluted further with 25 ml of ethyl acetate
  6. concentrationthe combined filtrates were concentrated under reduced pressure
  7. customRecrystallization of the residue from 95% ethanol
  8. customgave a light yellow powder (104.6 mg, 0.3348 mmol 33%), m.p. 114-120° C.

Sources & evidence

ORD record
ord-b226d4da40c3462a85f7a4c72ec4be8a
Source dataset
uspto-grants-2001_12
Patent number
US06331534B1

Reaction notes

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