Reaktion #6026

ord-41017e4fa30246a4918c64d6a34e9480

Reaktionsgleichung

C=CCc1cc(C(=O)OC)cc(CC=C)c1O
product
C=CCc1cc(C(=O)OC)cc(CC=C)c1O
methyl 4-hydroxy-3,5-di(2-propen-1-yl)benzoate
CC(C)(C)[Si](C)(C)Cl
tert-butyldimethylsilyl chloride
CCN(CC)CC
triethylamine
→
C=CCc1cc(C(=O)OC)cc(CC=C)c1O[Si](C)(C)C(C)(C)C
title compound
Ausbeute 97.2%
C=CCc1cc(C(=O)OC)cc(CC=C)c1O[Si](C)(C)C(C)(C)C
methyl 4-tert-butyldimethylsilyloxy-3,5-di(2-propen-1-yl)benzoate
Ausbeute 97.2%

Edukte

C=CCc1cc(C(=O)OC)cc(CC=C)c1O
product
C=CCc1cc(C(=O)OC)cc(CC=C)c1O
methyl 4-hydroxy-3,5-di(2-propen-1-yl)benzoate
CC(C)(C)[Si](C)(C)Cl
tert-butyldimethylsilyl chloride
CCN(CC)CC
triethylamine

Reagenzien

CN(C)c1ccncc1
DMAP

Lösungsmittel

ClCCl
dichloromethane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    EinengenThe mixture was concentrated
  2. 2
    Sonstigeflash chromatographed with 5%

Vorschrift

The product of Step B (3.1 g, 13.36 mmol) was treated with tert-butyldimethylsilyl chloride (2.22 g, 1.1 equiv), triethylamine (3 mL) and DMAP (0.1 equiv) in dichloromethane overnight. The mixture was concentrated and flash chromatographed with 5% and then 10% ethyl acetate in hexane to furnish 4.5 g (97%) of the title compound.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05246944uspto-grants-1993_09