Reaktion #305441

Reaktionsgleichung

water

Tetrabutylammonium fluoride

32

1,2,3-Tri(t-butyldimethylsilyloxy)-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-benzene

acetic acid

→

crude product

Ausbeute 122.9%

2,3,4-Trihydroxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-benzene

Ausbeute 122.9%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to 0° C.
2. 2
   ExtraktionThe reaction mixture was extracted with TBME (3×)
3. 3
   Trocknenthe organic phase was dried (Na2SO4)
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe residue was partitioned between CH3CN and cyclohexane
6. 6
   Sonstigethe CH3CN layer was separated
7. 7
   Einengenconcentrated in vacuo

Vorschrift

Tetrabutylammonium fluoride (1.37 mL, 1.37 mmol, 1M in THF) was added to a solution of 32 (0.45 g, 0.69 mmol) and glacial acetic acid (78 μL, 1.37 mmol) in THF (6 mL) at 0° C. The reaction mixture was allowed to warm to room temperature overnight, then cooled to 0° C. and water was added. The reaction mixture was extracted with TBME (3×) and the organic phase was dried (Na2SO4) and concentrated in vacuo. The residue was partitioned between CH3CN and cyclohexane and the CH3CN layer was separated and concentrated in vacuo to give the crude product (0.27 g). Purification by column chromatography (SiO2 1:1 EtOAc:cyclohexane) gave ZSB-79 (0.127 g, 58%) as a 86:14 mixture of Z:E isomers:

Quelle