Pyridine → Ethyl 9-ethylenedioxy-15-oxo-prostanoate

HRID 328515Notes

Reaction equation

HRID 328515 reaction equation
N1C=CC=CC=1.[CH2:7]1[CH2:26][O:25][CH:24]2[CH:9]([C@@H:10]([C@@H:22]([CH2:27][CH2:28][CH:29]([OH:35])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:23]2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[O:8]1>[O-2].[O-2].[O-2].[Cr+6].C(Cl)Cl>[CH2:7]1[CH2:26][O:25][CH:24]2[CH:9]([C@@H:10]([C@@H:22]([CH2:27][CH2:28][C:29](=[O:35])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:23]2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[O:8]1

Participants

5

Reactant 2

HCID 1049PyridineHCID 68124126Ethyl 9-ethylenedioxy-15-hydroxy-prostanoate

Product 1

HCID 68123704Ethyl 9-ethylenedioxy-15-oxo-prostanoate

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 8.7 g. of dry pyridine in 140 ml. of dry methylene chloride, stirred in a tap water bath is treated with 5.5 g. of dry chromium trioxide. The resulting deep red suspension is stirred at ambient temperature for 15 minutes. A solution of 3.78 g. of ethyl-9-ethylenedioxy-15-hydroxy-prostanoate (Example 55) in 15 ml. of methylene chloride is added, all at once, to the suspension. A black, tarry deposit is formed immediately. After stirring for 15 minutes at ambient temperature, the methylene chloride solution is decanted from the tarry deposit which is triturated with several portions of ether. The combined organic phases are washed with 5% aqueous sodium hydroxide, water, ice-cold 5% aqueous hydrochloric acid, saturated sodium bicarbonate solution, and saturated sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness to give 3.29 g. (88%) of a viscous oil; λ max 5.78 and 5.86 μ (carbonyl groups).

Workup

  1. additionis treated with 5.5 g
  2. customA black, tarry deposit is formed immediately
  3. stirringAfter stirring for 15 minutes at ambient temperature
  4. customthe methylene chloride solution is decanted from the tarry deposit which
  5. customis triturated with several portions of ether
  6. washThe combined organic phases are washed with 5% aqueous sodium hydroxide, water, ice-cold 5% aqueous hydrochloric acid, saturated sodium bicarbonate solution, and saturated sodium chloride solution
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customto give 3.29 g

Sources & evidence

ORD record
ord-4a0caaea599840c687553e2069377b68
Source dataset
uspto-grants-1977_04
Patent number
US04017534

Reaction notes

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