Methanol → 2-(1,2-Epoxy-1,5-dimethyl-4-hexenyl)-1-(2-hydroxymethylbenzyl)thiomethyl-3-methoxy-1,4-cyclohexanediol

HRID 1646653Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1646653
CO.C[O-].[Na+].[SH:6][CH2:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH2:10][OH:11].[CH3:16][C:17]([CH3:35])=[CH:18][CH2:19][C@H:20]1[O:22][C@@:21]1([C@@H:24]1[C@:29]2([O:31][CH2:30]2)[CH2:28][CH2:27][C@@H:26]([OH:32])[C@H:25]1[O:33][CH3:34])[CH3:23]>O>[O:22]1[CH:20]([CH2:19][CH:18]=[C:17]([CH3:35])[CH3:16])[C:21]1([CH:24]1[CH:25]([O:33][CH3:34])[CH:26]([OH:32])[CH2:27][CH2:28][C:29]1([CH2:30][S:6][CH2:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH2:10][OH:11])[OH:31])[CH3:23]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 222778FumagillolHCID 10942334Sodium MethoxideHCID 14708630[2-(Sulfanylmethyl)phenyl]methanol

Produkt 1

HCID 198009842-(1,2-Epoxy-1,5-dimethyl-4-hexenyl)-1-(2-hydroxymethylbenzyl)thiomethyl-3-methoxy-1,4-cyclohexanediolAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To an about 14% methanol solution (6 ml) of sodium methoxide were added, under ice-cooling, 2-mercaptomethylbenzylalcohol (655 mg) and fumagillol (1.00 g). The mixture was stirred for one hour at room temperature, to which was added water to suspend the reaction. The product was extracted with ethyl acetate, The extract solution was washed with a saturated aqueous solution of sodium chloride, then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by means of a silica gel column chromatography (carrier 30 g, developing solvent : ethyl acetate - hexane=2:1) to give 2-(1,2-epoxy-1,5-dimethy-4-hexenyl)-1-(2-hydroxymethylbenzyl)thiomethyl-3-methoxy-1,4-cyclohexanediol (1.43 g : yield 92%) as a colorless oily substance.

Aufarbeitung

  1. temperaturecooling
  2. customthe reaction
  3. extractionThe product was extracted with ethyl acetate
  4. washThe extract solution was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by means of a silica gel column chromatography (carrier 30 g, developing solvent : ethyl acetate - hexane=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-7614bbc01ad345b9b90f03994e3cb942
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05180735

Notizen zur Reaktion

Wird geladen…