Trioxobis(pyridine)chromium → Prostaglandin E2

HRID 1834052Notes

Reaction equation

HRID 1834052 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@@H:6]1[O:19][C:17](=[O:18])[CH2:16][CH2:15][CH2:14][CH:13]=[CH:12][CH2:11][C@H:10]2[C@@H:20]([OH:24])[CH2:21][C@@H:22]([OH:23])[C@@H:9]2[CH:8]=[CH:7]1.[O:25]=[Cr](=O)=O.C1C=CC=CN=1.C1C=CC=CN=1>C(Cl)Cl>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:19])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:10]([CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][C:17]([OH:25])=[O:18])[C:20](=[O:24])[CH2:21][C@H:22]1[OH:23]

Participants

4

Reactant 2

HCID 88565Trioxobis(pyridine)chromiumHCID 5283073PGF2α 1,15-lactone

Product 1

HCID 5280360Prostaglandin E2

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mono-trimethylsilyl derivative of PGF2α 1,15-lactone (above) was dissolved in 6 ml of methylene chloride and added in one portion to the rapidly stirred Collins reagent. The ice bath was removed and the reaction mixture was allowed to stir for 20 min. longer. The mixture was then poured onto a column containing 150 g of neutral silica. With the aid of a house-vacuum, the column was eluted into a 2-liter round bottom flask with 1000 ml of ethyl acetate. Removal of the solvent gave PGE2, 1,15-lactone, 11-trimethylsilyl ether.

Workup

  1. customThe ice bath was removed
  2. additionThe mixture was then poured onto a column
  3. additioncontaining 150 g of neutral silica
  4. washWith the aid of a house-vacuum, the column was eluted into a 2-liter round bottom flask with 1000 ml of ethyl acetate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-ebbb2b8e177e4289a215698e939951b7
Source dataset
uspto-grants-1978_01
Patent number
US04067991

Reaction notes

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