Phosphorus oxychloride → 9-Oxo-8(12),13-trans-prostadienoic acid

HRID 973189Notes

Reaction equation

HRID 973189 reaction equation
O[C@@H:2]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])/[CH:3]=[CH:4]/[C:5]1[CH2:6][CH2:7][C:8](=[O:19])[C:9]=1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17].C(OC=C(OC(C)=COC(C)C)C)(C)C.P(Cl)(Cl)(Cl)=O>C(Cl)Cl.CCOCC>[O:19]=[C:8]1[CH2:7][CH2:6][C:5](/[CH:4]=[CH:3]/[CH2:2][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17]

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 5280388Pgb1HCID 88809635Isopropoxyisopropenyl ether

Product 1

HCID 867351629-Oxo-8(12),13-trans-prostadienoic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a 250 ml roundbottom borosilicate flask containing 0.4 g of 15(S)-hydroxy-9-oxo-8(12),13-trans-prostadienoic acid in 15 ml of methylene chloride is added 5 ml of isopropoxyisopropenyl ether and 0.01 ml of phosphorus oxychloride and the flask's contents allowed to react at 20° C for 36 hours. Next, the reaction product is diluted with 25 ml of ether and washed with 50% brine and saturated brine until the solution is neutral. Next, the residue is extracted with methylene chloride, filtered, and freed of solvent under reduced pressure, dried over anhydrous magnesium sulfate, the give 15(S)-(dimethyl' isopropoxy' methyloxy)-9-oxo-8(12),13-trans-prostadienoic acid.

Workup

  1. customto react at 20° C for 36 hours
  2. washwashed with 50% brine and saturated brine until the solution
  3. extractionNext, the residue is extracted with methylene chloride
  4. filtrationfiltered
  5. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-07ff0f155dd14390891f532ef12be06a
Source dataset
uspto-grants-1977_10
Patent number
US04055593

Reaction notes

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