Reaktion #43283

Reaktionsgleichung

ammonium chloride

triethylamine

3-iodobenzyl alcohol

methyl acrylate

methyl acrylate

triethylamine

→

compound 17

Ausbeute 97.0%

(E)-3-(3-Hydroxymethyl-phenyl)-acrylic acid methyl ester

Ausbeute 97.0%

Lösungsmittel

CH3CN

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigescrew-cap
2. 2
   Temperaturto cool to room temperature
3. 3
   TemperaturThe reaction was heated at 100° C. overnight
4. 4
   ExtraktionThe resulting mixture was extracted with dichloromethane (3×40 mL)
5. 5
   Trocknenthe combined dichloromethane solution was dried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   SonstigePurification by flash chromatography on silica gel (30% ethyl acetate/hexanes)

Vorschrift

The procedure described in Reich, S. H. etal. J. Med. Chem. 2000, 43, 1670 was followed. Pd(OAc)2 (8.2 mg, 0.037 mmol) and triethylamine (0.360 mL, 2.58 mmol) were added to a solution of 3-iodobenzyl alcohol 15 (0.27 mL, 2.13 mmol) and methyl acrylate 16 (0.220 mL, 2.44 mmol) in CH3CN (4.5 mL). The reaction vessel was sealed with a Teflon screw-cap and was heated at 100° C. for 5 h. At this time, the reaction was allowed to cool to room temperature and the tube was charged with 0.22 mL more of methyl acrylate, 11.7 mg Pd(OAc)2 and 0.360 mL triethylamine. The reaction was heated at 100° C. overnight and then 10 mL saturated ammonium chloride solution was added. The resulting mixture was extracted with dichloromethane (3×40 mL) and the combined dichloromethane solution was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (30% ethyl acetate/hexanes) gave 395 mg (97%) of compound 17.

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