Isopropanol → HCID 86744831, compound

HRID 1493647Notes

Reaction equation

HRID 1493647 reaction equation
[O:1]=[C:2]([CH2:10][C@@H:11]1[C@@H:15](/[CH:16]=[CH:17]/[C@@H:18]([O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[CH:19]([CH3:24])[CH2:20][C:21]#[C:22][CH3:23])[C@H:14]([O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[CH2:13][C@@H:12]1[OH:39])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].C(O)(C)C>CC(C)=O>[O:1]=[C:2]([CH2:10][C@@H:11]1[C@@H:15](/[CH:16]=[CH:17]/[C@@H:18]([O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[CH:19]([CH3:24])[CH2:20][C:21]#[C:22][CH3:23])[C@H:14]([O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[CH2:13][C:12]1=[O:39])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 86744832HCID 86744832, compound

Product 1

HCID 86744831HCID 86744831, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The solution of 396 mg of (13E)-(9S,11R,15S,16RS)-6-oxo-9-hydroxy-11,15-bis-(tetrahydropyran-2-yloxy)-16-methyl-18,18,19,19-tetradehydro-13-prostenoic acid in 8 ml of absolute dimethylketone was cooled, with exclusion of moisture, to -30° C., was mixed with 270 microliters of Jones solution and stirred for 1.5 h at -30° C. to -20° C. After addition of 2 ml of isopropanol, it was poured onto 50 ml of ice water, extracted several times with a total of 100 ml of diethyl ether, washed neutral with saturated sodium chloride solution, dried on magnesium sulfate, filtered and concentrated by evaporation in a vacuum. The colorless raw oil was chromatographed on plates coated with silica gel with hexane-ethyl acetate. Besides the initial material, 160 mg (41%) of the title compound was isolated as colorless oil.

Workup

  1. additionwas mixed with 270 microliters of Jones solution
  2. extractionextracted several times with a total of 100 ml of diethyl ether
  3. washwashed neutral with saturated sodium chloride solution
  4. customdried on magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation in a vacuum
  7. customThe colorless raw oil was chromatographed on plates

Sources & evidence

ORD record
ord-4bce090ef20a49e4929f42a9bd66e79d
Source dataset
uspto-grants-1991_06
Patent number
US05023273

Reaction notes

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