(2S-trans)-2,3-bis[(benzyloxy)methyl]cyclobutanone → Dibenzyl ether

HRID 36093

Reaktionsgleichung

Reaktionsgleichung von HRID 36093
C(O[CH2:9][C@@H:10]1[C@@H:13]([CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][C:11]1=O)C1C=CC=CC=1.[CH2:24]([Al](CC(C)C)CC(C)C)C(C)C>C1(C)C=CC=CC=1>[CH2:16]([O:15][CH2:14][C:13]1[CH:10]=[CH:9][CH:24]=[CH:11][CH:12]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

4

Edukt 2

HCID 14863583(2S-trans)-2,3-bis[(benzyloxy)methyl]cyclobutanoneHCID 16682931Triisobutylaluminum2×

Produkt 1

HCID 7657Dibenzyl ether

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

A solution of (2S-trans)-2,3-bis[(benzyloxy)methyl]cyclobutanone (0.2 g., 0.645 mmole) in toluene (4 ml.) was added dropwise over 10 minutes to a solution of triisobutylaluminum (0.91 M in hexane, 0.9 ml., 0.816 mmole) in toluene (2 ml.) at -40° C. The mixture was stirred at -50° C. for 4 hours and at -40° C. for one hour. A solution of triisobutylaluminum (1 ml., 0.91 mmole) was added to the reaction mixture. After stirring for 30 minutes the reaction was quenched by adding 10% hydrochloric acid (2 ml.) at -40° C. The organic phase was washed with brine, dried (magnesium sulfate), and the solvent was evaporated to give [1S-(1α,2β,3β)]-3-hydroxy-1,2-cyclobutanedimethanol, dibenzyl ether; TLC (30% ethyl acetate/hexane) Rf =0.3. The product contained about 5% of the isomeric compound; TLC (30% ethyl acetate/hexane) Rf =0.2.

Aufarbeitung

  1. stirringAfter stirring for 30 minutes the reaction
  2. customwas quenched
  3. additionby adding 10% hydrochloric acid (2 ml.) at -40° C
  4. washThe organic phase was washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-4dfa1debe66d46a791cd9e5f90acd2c9
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05412134

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