Water → (3-Methoxyphenyl)(2-(2,4,6-trimethoxybenzylthio)phenyl)methanol

HRID 1158203

Reaktionsgleichung

Reaktionsgleichung von HRID 1158203
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:9][C:10]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([O:18][CH3:19])=[CH:12][C:11]=1[O:20][CH3:21].[Li]CCCC.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH:32]=[O:33].O>C1COCC1.CCCCCC.C(OCC)(=O)C>[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:32]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8][CH2:9][C:10]2[C:15]([O:16][CH3:17])=[CH:14][C:13]([O:18][CH3:19])=[CH:12][C:11]=2[O:20][CH3:21])[OH:33])[CH:34]=[CH:35][CH:36]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 115693-MethoxybenzaldehydeHCID 66870845(2-Bromophenyl)(2,4,6-trimethoxybenzyl)sulfaneHCID 178418339Butyllithium

Produkt 1

HCID 68643652(3-Methoxyphenyl)(2-(2,4,6-trimethoxybenzylthio)phenyl)methanolAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

To a solution of 0.35 g (2-bromophenyl)(2,4,6-trimethoxybenzyl)sulfane (0.96 mmol) in dry THF was added slowly 1.2 eq n-BuLi. The reaction was stirred 25 minutes at −78° C. before 1.2 eq 3-methoxybenzaldehyde was added slowly. The reaction was warmed to ambient temperature and stirred for one additional hour before the addition of water. The mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Flash silica chromatography (hexane:ethyl acetate 80:20) afforded 0.288 g product (0.68 mmol, 70% yield).

Aufarbeitung

  1. additionwas added slowly
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e9e4de51aafc4a4f99f02489027f754c
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807713B2

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