Water → Prostaglandin D2

HRID 328230

Reaction equation

HRID 328230 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C@@H:12]([OH:23])[CH2:11][C@H:10]1[OH:24].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C.O>CC(C)=O.C(OCC)C>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@H:9]1[C:10](=[O:24])[CH2:11][C@H:12]([OH:23])[C@@H:13]1[CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21]

Participants

7

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 5280363DinoprostHCID 131709961Jones' reagent

Product 1

HCID 448457Prostaglandin D2

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

PGF2α, 15-(tetrahydropyranyl ether) (2 g.) in acetone (75 ml.) is cooled to -45° C. and thereafter treated with 1.2 ml. of the Jones reagent. The mixture is stirred for 30 min. at -35° to -45° C. and thereafter treated with 0.5 ml. of isopropanol and stirred an additional 15 min. The reaction mixture is then poured into a mixture of ice, water, and diethyl ether. The mixture is then extracted with diethyl ether and the combined ethereal extracts washed with brine, and dried over sodium sulfate. After filtration removal of solvent proceeds by rotary evaporation. Crude product (1.8 g.) thereby obtained is chromatographed on 360 g. of acid washed silica gel eluting with 45 percent ethyl acetate in hexane. PGD2, 15-(tetrahydropyranyl ether) (800 mg.) is thereby obtained.

Workup

  1. additiontreated with 1.2 ml
  2. additiontreated with 0.5 ml
  3. extractionThe mixture is then extracted with diethyl ether
  4. washthe combined ethereal extracts washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration removal of solvent proceeds
  7. customby rotary evaporation
  8. customCrude product (1.8 g.) thereby obtained
  9. customis chromatographed on 360 g
  10. washof acid washed silica gel eluting with 45 percent ethyl acetate in hexane

Sources & evidence

ORD record
ord-9eb8f68d657a448a81c0d8006840963f
Source dataset
uspto-grants-1977_04
Patent number
US04016184

Linked notes

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