8-methylsulfonyl-12(S)-hydroxy-10-heptadecynoic acid → 8-methylsulfonyl-12(S)-hydroxyheptadecanoic acid

HRID 263009Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 263009
[CH3:1][S:2]([CH:5]([CH2:15][C:16]#[C:17][C@@H:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])(=[O:4])=[O:3].[H][H]>[Pt].C(OCC)(=O)C.C1CCCCC1>[CH3:1][S:2]([CH:5]([CH2:15][CH2:16][CH2:17][C@@H:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])(=[O:3])=[O:4]

Komponenten

6

Edukt 2

HCID 227969758-methylsulfonyl-12(S)-hydroxy-10-heptadecynoic acidHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 227969768-methylsulfonyl-12(S)-hydroxyheptadecanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23939PlatinumKatalysatorHCID 8078CyclohexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

8-Methylsulfonyl-12(S)-hydroxy-10-heptadecynoic acid (36.0 g., 0.10 mole) and 5% platinum-on-charcoal catalyst (4.0 g.) are placed in a mixture of ethyl acetate (100 ml.) and cyclohexane (200 ml.) and hydrogenated in a Parr apparatus with an initial hydrogen pressure of 45 pounds per square inch. The uptake of the required 0.2 mole of hydrogen is complete in 20 minutes. The catalyst is removed by filtration and the solvents evaporated to leave the product as a residual oil weighing 33.5 g. It is purified by chromatography on silica gel with benzene-dioxane-acetic acid elution. The title compound is obtained as a nearly colorless viscous oil.

Aufarbeitung

  1. customThe catalyst is removed by filtration
  2. customthe solvents evaporated

Quellen und Nachweise

ORD-Eintrag
ord-d3de8fcd40ae4955b22a7d9023af86ac
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04155908

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