Tetrahydrofuran → HCID 178444448, Verbindung

HRID 1590519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1590519
[Br-].[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:11][CH:10]=1.[CH2:37]([C@H:42]1[CH2:47][CH2:46][C@H:45]([CH:48]=O)[CH2:44][CH2:43]1)[CH2:38][CH2:39][CH2:40][CH3:41].O1CCCC1>O>[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH:17]=[CH:48][C@H:45]2[CH2:46][CH2:47][C@H:42]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:43][CH2:44]2)=[CH:13][CH:14]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 18471791[3-(4-[2-Tetrahydropyranyloxy]phenyl)propyl]triphenylphosphonium bromideHCID 178444538HCID 178444538, Verbindung

Produkt 1

HCID 178444448HCID 178444448, VerbindungAusbeute 36,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4.0 g of [3-(4-[tetrahydro-2-pyranyloxy]phenyl)-1-propyl]triphenylphosphonium bromide, 1.3 g of trans-4-pentylcyclohexanecarboxaldehyde and 50 ml of absolute tetrahydrofuran was treated portionwise with 0.8 g of solid potassium t-butylate. After completion of the addition the reaction mixture was stirred for a further two hours and then poured into 500 ml of water and extracted three times with 100 ml of diethyl ether each time. The organic phases were washed twice with 500 ml of concentrated sodium chloride solution each time, dried over magnesium sulphate, filtered and subsequently concentrated. Chromatography of the residue on silica gel with toluene gave 1.0 g of 1-[tetrahydro-2-pyranyloxy]-4-[4-(trans-4-pentylcyclohexyl)-3-butenyl]benzene (cis/trans mixture).

Aufarbeitung

  1. additionAfter completion of the addition the reaction mixture
  2. extractionextracted three times with 100 ml of diethyl ether each time
  3. washThe organic phases were washed twice with 500 ml of concentrated sodium chloride solution each time
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationsubsequently concentrated

Quellen und Nachweise

ORD-Eintrag
ord-d792382d78724dcfb04306b60684f429
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05204018

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