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

HRID 439899

Reaktionsgleichung

Reaktionsgleichung von HRID 439899
C([O:8][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:23])C1C=CC=CC=1.[Cl-].[Cl-].[CH2:26]([Al+2])C(C)C>C1(C)C=CC=CC=1>[OH:23][CH:11]1[CH2:12][CH:13]([CH2:14][OH:15])[CH:10]1[CH2:9][OH:8].[CH2:16]([O:15][CH2:14][C:13]1[CH:10]=[CH:9][CH:26]=[CH:11][CH:12]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

5

Edukt 2

HCID 14863583(2S-trans)-2,3-bis[(benzyloxy)methyl]cyclobutanoneHCID 166861082-Methylpropylaluminum(2+) dichloride

Produkt 2

HCID 7657Dibenzyl etherHCID 540835352,3-Bis(hydroxymethyl)cyclobutanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of (2S-trans) -2,3-bis [(benzyloxy)-methyl]cyclobutanone (0.5 g., 1.61 mmole) in toluene (1 ml. ) was added dropwise to a solution of isobutylaluminum dichloride (0.71 M in hexane, 3.41 ml., 2.42 mmole) at -78° C. The mixture was allowed to warm slowly to room temperature over 2 hours. After stirring for 30 minutes at room temperature, the mixture was allowed to stand at 0° C. overnight. After dilution with ethyl acetate, the reaction mixture was quenched with 10% hydrochloric acid. The organic phase was washed with brine, dried (magnesium sulfate) and the solvent evaporated to give [1S-(1α, 2β, 3β)]-3-hydroxy-1,2-cyclobutanedimethanol, dibenzyl ether; TLC (50% ethyl acetate/hexane ) Rf =0.53.

Aufarbeitung

  1. waitto stand at 0° C. overnight
  2. customAfter dilution with ethyl acetate, the reaction mixture was quenched with 10% hydrochloric acid
  3. washThe organic phase was washed with brine
  4. dry with materialdried (magnesium sulfate)
  5. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-298f048a039140f3b37ba50256894601
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05516903

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