Sodium Chloride → trans 4-(4-Methoxy-benzyloxy)-but-2-en-1-ol

HRID 1784055

Reaktionsgleichung

Reaktionsgleichung von HRID 1784055
[CH2:1]([OH:6])/[CH:2]=[CH:3]/[CH2:4][OH:5].[H-].[Na+].[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Cl)=[CH:13][CH:12]=1.[Na+].[Cl-]>CN(C=O)C>[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][O:5][CH2:4]/[CH:3]=[CH:2]/[CH2:1][OH:6])=[CH:13][CH:12]=1

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 175854trans-2-Butene-1,4-diol

Produkt 1

HCID 5371004trans 4-(4-Methoxy-benzyloxy)-but-2-en-1-olAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 11.8 g (133.4 mmol) of trans 2-butene-1,4-diol in 100 ml of DMF was treated with 6.4 g (147 mmol) of sodium hydride dispersion on oil (55%), stirred at 0° C. for 45 min., and treated dropwise with 25.1 g (160 mmol) of 4-methoxybenzylchloride. The mixture was stirred during 5 hrs at RT and then poured into a saturated aqueous solution of NaCl. Extraction with AcOEt, drying of the combined organic phases over Na2SO4, filtration, evaporation of the solvent and chromatography on silica gel with heptane/AcOEt 9:1 gave 5.7 g (21%) of trans 4-(4-methoxy-benzyloxy)-but-2-en-1-ol. Light yellow oil. MS: 207 (M−H)−.

Aufarbeitung

  1. stirringThe mixture was stirred during 5 hrs at RT
  2. extractionExtraction with AcOEt
  3. dry with materialdrying of the combined organic phases over Na2SO4, filtration, evaporation of the solvent and chromatography on silica gel with heptane/AcOEt 9:1

Quellen und Nachweise

ORD-Eintrag
ord-228c5fc2707a43a489978db56dbc3af7
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07501413B2

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