Tetrahydropyranyl ether → Tetrahydropyranyl ether

HRID 1395808

Reaction equation

HRID 1395808 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:26])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14][C:15]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:16])[C@@H:12]([OH:24])[CH2:11][C@H:10]1[OH:25].[O:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]1[O:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][O:35]1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:26])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14][C:15]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:16])[C:12](=[O:24])[CH2:11][C@H:10]1[OH:25].[O:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]1[O:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][O:35]1

Participants

6

Reactant 3

HCID 263182Tetrahydropyranyl etherHCID 52808886-Ketoprostaglandin F1 alphaHCID 131709961Jones' reagent

Product 2

HCID 263182Tetrahydropyranyl etherHCID 52808896-Keto-PGE1

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The reaction product from part A, containing 6-keto-PGF1α, bis(tetrahyropyranyl)ether, methyl ester corresponding to formula IV, is oxidized to compound V. A composite from several lots, weighing 0.93 g., in 20 ml. of acetone is treated at -10° C. with 2.0 ml. of Jones reagent. After stirring for 1.5 hr. the reaction mixture is quenched with isopropanol and extracted with diethyl ether. The extract is washed with brine, dried, and concentrated. The residue is subjected to silica gel chromatography, eluting with ethyl acetate (20-50%)-Skellysolve B to yield the formula-V 6-keto-PGE1, bis(tetrahydropyranyl)ether, methyl ester, 0.52 g., having Rf 0.52 (TLC on silica gel in ethyl acetate-Skellysolve B (1:1)); and infrared peaks at 1745 and 1725 cm-1 (free of OH at 3000-3500).

Workup

  1. customthe reaction mixture is quenched with isopropanol
  2. extractionextracted with diethyl ether
  3. washThe extract is washed with brine
  4. customdried
  5. concentrationconcentrated
  6. washeluting with ethyl acetate (20-50%)-Skellysolve B

Sources & evidence

ORD record
ord-97eeed0a44514c299a7f39068ff6ad16
Source dataset
uspto-grants-1980_05
Patent number
US04205178

Linked notes

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