2-Heptanone, 1-(triphenylphosphoranylidene)- → 2-(7-Hydroxyheptyl)-3-(3-oxooct-1-enyl)-5-(2-tetrahydropyranyloxy)cyclopentanol

HRID 1580791Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1580791
[CH:1]([CH:3]1[CH2:7][CH:6]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[CH:5]([OH:15])[CH:4]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23])=O.[C:24]([CH:31]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>O1CCCC1>[OH:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH:4]1[CH:3]([CH:1]=[CH:31][C:24](=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:7][CH:6]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[CH:5]1[OH:15]

Komponenten

4

Edukt 2

HCID 107619442-Heptanone, 1-(triphenylphosphoranylidene)-HCID 203548513-Formyl-2-(7-hydroxyheptyl)-5-(2-tetrahydropyranyloxy)cyclopentanol

Produkt 1

HCID 867329952-(7-Hydroxyheptyl)-3-(3-oxooct-1-enyl)-5-(2-tetrahydropyranyloxy)cyclopentanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 3-formyl-2-(7-hydroxyheptyl)-5-(2-tetrahydropyranyloxy)cyclopentanol [5.4 g.; prepared as described above in Example 2(e)] and hexanoylmethylene triphenylphosphorane (5.6 g.) in dry tetrahydrofuran (60 ml.) was heated under reflux under nitrogen for 24 hours. The solvent was then removed in vacuo and the resulting residue was chromatographed on silica gel. Elution with diethyl ether gave 2-(7-hydroxyheptyl)-3-(3-oxooct-1-enyl)-5-(2-tetrahydropyranyloxy)cyclopentanol (3.64g.),νmax 3450 cm-1, 1670 cm-1, 1630 cm-1, 985 cm-1.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux under nitrogen for 24 hours
  3. customThe solvent was then removed in vacuo
  4. customthe resulting residue was chromatographed on silica gel
  5. washElution with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-93b5afbfdf744708a6388d77870c23e7
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03933890

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