Tetrahydrofuran → 1,1'-{[4-(Prop-1-en-2-yl)-1,3-phenylene]bis(oxymethylene)}dibenzene

HRID 1891170Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1891170
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[C:23](=O)[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[C:23]([CH3:24])=[CH2:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 8028Tetrahydrofuran2×HCID 3194691-(2,4-Bis(benzyloxy)phenyl)ethanone

Produkt 1

HCID 247733591,1'-{[4-(Prop-1-en-2-yl)-1,3-phenylene]bis(oxymethylene)}dibenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 74505Methyltriphenyliphosphonium bromideKatalysator

Versuchsvorschrift

Methyltriphenylphosphonium bromide (1.1 eq) was suspended in an. THF and cooled to 0° C. under nitrogen. 1.6M nButyllithium in hexanes (1.1 eq) was added drop wise, and stirred for 30 minutes. 1-(2,4-Bis-benzyloxy-phenyl)-ethanone (1 eq) was dissolved in an. THF and added drop wise to the suspension. When addition was completed, the ice bath was removed and the reaction mixture was stirred at room temperature under nitrogen overnight. Methanol was added to the reaction mixture and the resulting solution was evaporated in vacuo. Hexane was added to the resulting oil and heated to reflux for 30 minutes, then filtered through Celite. The liquor was evaporated in vacuo to give an oil which was purified by column chromatography, eluting with 30% EtOAc in hexane, to give 2,4-Bis-benzyloxy-1-isopropenyl-benzene.

Aufarbeitung

  1. additionWhen addition
  2. customthe ice bath was removed
  3. stirringthe reaction mixture was stirred at room temperature under nitrogen overnight
  4. additionMethanol was added to the reaction mixture
  5. customthe resulting solution was evaporated in vacuo
  6. additionHexane was added to the resulting oil
  7. temperatureheated
  8. temperatureto reflux for 30 minutes
  9. filtrationfiltered through Celite
  10. customThe liquor was evaporated in vacuo
  11. customto give an oil which
  12. customwas purified by column chromatography
  13. washeluting with 30% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-251b9fd0d48a4cc4b0b9af2492455588
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507480B2

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