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

HRID 1764189

Reaction equation

HRID 1764189 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, to 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-4b084dce544449258417b09d4d8744d2
Source dataset
uspto-grants-1978_09
Patent number
US04115545

Linked notes

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