Diethyl Ether → HCID 53703346, compound

HRID 864365Notes

Reaction equation

HRID 864365 reaction equation
[CH3:1][C:2]([C@@H:5]1[C@:22]2([CH3:23])[C@H:8]([C@H:9]3[C@H:19]([CH2:20][CH2:21]2)[C@:17]2([CH3:18])[C:12]([CH2:13][C@@H:14]([OH:24])[CH2:15][CH2:16]2)=[CH:11][CH2:10]3)[CH2:7][CH2:6]1)=[CH:3][CH3:4].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC>C(Cl)Cl>[CH3:1][C:2]([C@@H:5]1[C@:22]2([CH3:23])[C@H:8]([C@H:9]3[C@H:19]([CH2:20][CH2:21]2)[C@:17]2([CH3:18])[C:12](=[CH:13][C:14](=[O:24])[CH2:15][CH2:16]2)[CH2:11][CH2:10]3)[CH2:7][CH2:6]1)=[CH:3][CH3:4]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 57236229HCID 57236229, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 53703346HCID 53703346, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20,21-Dimethylpregna-5,20-dien-3β-ol (6,400.3 mg, 1.218 mmol) in 5 mL of methylene chloride was oxidized with pyridinium chlorochromate (525.4 mg 2.437 mmol) for 42 h. Ether (3.5 mL) was added and the suspension was filtered through a 5 mm dia.×60 mm high column of silica gel. The column was further eluted with 3.5 mL of ether and the combined filtrates were concentrated under reduced pressure. Flash chromatography of the resin followed by recrystallization from aqueous ethanol gave yellow crystals (43.6 mg, 0.134 mmol 11%). m.p. 157°-165° C. (NA-1993B-84)

Workup

  1. filtrationthe suspension was filtered through a 5 mm dia
  2. washThe column was further eluted with 3.5 mL of ether
  3. concentrationthe combined filtrates were concentrated under reduced pressure
  4. customFlash chromatography of the resin followed by recrystallization from aqueous ethanol
  5. customgave yellow crystals (43.6 mg, 0.134 mmol 11%)

Sources & evidence

ORD record
ord-f0cb7a7ee6ff42cdbaabc507921e8b22
Source dataset
uspto-grants-1996_10
Patent number
US05563131

Reaction notes

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