Diethyl Ether → HCID 53703346, compound

HRID 2270514Notes

Reaction equation

HRID 2270514 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 l1). m.p. 157-165° C.

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 l1)

Sources & evidence

ORD record
ord-02aa0ec4c9be4f1888ba242a1be43827
Source dataset
uspto-grants-2001_12
Patent number
US06331534B1

Reaction notes

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