Hydrochloric Acid → methyl 3(RS)-hydroxy-2-(3(RS)-[tetrahydropyran-2-yl]oxy-1-octynyl)-5-oxocyclopentane-heptanoate

HRID 918276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 918276
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:9]#[CH:10].C([Li])CCC.[Cl-].[Cl-].[Cl-].[Al+3].[OH:25][CH:26]1[CH2:30][C:29](=[O:31])[C:28]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])=[CH:27]1.Cl>CCCCCC.CCOCC>[OH:25][CH:26]1[CH2:30][C:29](=[O:31])[CH:28]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])[CH:27]1[C:10]#[C:9][CH:8]([O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 3912664NorprostolHCID 6451240Aluminum(III) ChlorideHCID 117890622H-Pyran, 2-[(1-ethynylhexyl)oxy]tetrahydro-HCID 178418339Butyllithium

Produkt 1

HCID 21521713methyl 3(RS)-hydroxy-2-(3(RS)-[tetrahydropyran-2-yl]oxy-1-octynyl)-5-oxocyclopentane-heptanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel3×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of 1.47 parts of 3(RS)-(tetrahydropyran-2-yl)oxy-1-octyne in 7.1 parts of ether is treated at -40° with 2.6 parts by volume of a 2.3 M butyl lithium in hexane solution. The reaction mixture is stirred at room temperature for 1 hour, then cooled to -40°. 0.267 Part of aluminum trichloride is added and the mixture is stirred at room temperature for 2 hours. After that time, 0.240 part of methyl 3(RS)-hydroxy-5-oxocyclopent-1-eneheptanoate, dissolved in ether, is added and the resulting mixture is stirred at room temperature for about 16 hours. The reaction mixture then is poured into a mixture of 35.5 parts of ether and 20 parts by volume of an aqueous 0.5 N hydrochloric acid solution. The ethereal layer is separated, washed with water, dried over anhydrous sodium sulfate and stripped of solvent. The remaining material is chromatographed on silica gel with 20% ethyl acetate in benzene as eluent to yield, as a stereoisomeric mixture, methyl 3(RS)-hydroxy-2-(3(RS)-[tetrahydropyran-2-yl]oxy-1-octynyl)-5-oxocyclopentane-heptanoate.

Aufarbeitung

  1. temperaturecooled to -40°
  2. stirringthe mixture is stirred at room temperature for 2 hours
  3. additionis added
  4. stirringthe resulting mixture is stirred at room temperature for about 16 hours
  5. customThe ethereal layer is separated
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe remaining material is chromatographed on silica gel with 20% ethyl acetate in benzene as eluent

Quellen und Nachweise

ORD-Eintrag
ord-fefec2e382e4426a97425c11cd7e1324
Quelldatensatz
uspto-grants-1976_07
Patentnummer
US03970683

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