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

HRID 372132Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 372132
[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)cyclopentanolAusbeute 57,3 %

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 (3.64 g.), 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-2cf05fe8936c480e83d7e55985fca195
Quelldatensatz
uspto-grants-1978_05
Patentnummer
US04088821

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