Diethyl Ether → HCID 70548043, compound

HRID 2058437Notes

Reaction equation

HRID 2058437 reaction equation
[C:1]([CH:9]1[C:26](=[O:27])[CH2:25][CH2:24][C@@:23]2([CH3:28])[C@H:10]1[CH2:11][CH2:12][C@@H:13]1[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@H:14]1[CH2:15][CH2:16][C@@H:17]2[OH:29])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC>C(Cl)Cl>[C:1]([CH:9]1[C:26](=[O:27])[CH2:25][CH2:24][C@@:23]2([CH3:28])[C@H:10]1[CH2:11][CH2:12][C@@H:13]1[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@H:14]1[CH2:15][CH2:16][C:17]2=[O:29])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 12837419HCID 12837419, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 70548043HCID 70548043, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Benzoyl-17β-hydroxy-5α-androstan-3-one made as in Example 1 (788 mg, 2 mmole) in 2 ml of CH2Cl2 is added to pyridinium chlorochromate (650 mg, 3 mmole) suspended in CH2Cl2 (2 ml) at 25° C. After 2 hours, ether is added and the solvent decanted. This is then filtered through Florisil, the eluate evaporated and the residue recrystallized from chloroform-heptane.

Workup

  1. customthe solvent decanted
  2. filtrationThis is then filtered through Florisil
  3. customthe eluate evaporated
  4. customthe residue recrystallized from chloroform-heptane

Sources & evidence

ORD record
ord-fc21f790440a4e4fbbc7bb8a1a312616
Source dataset
uspto-grants-1982_03
Patent number
US04317817

Reaction notes

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