Water → Prostaglandin D2

HRID 1112552Notes

Reaction equation

HRID 1112552 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

Conditions

Temperature
-40 °C

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 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

Sources & evidence

ORD record
ord-73d7a595110e4973a4c1e1d5f654f8a2
Source dataset
uspto-grants-1978_10
Patent number
US04122282

Reaction notes

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