反応 #815245

反応方程式

diethyl carbonate

3-methoxy-5-methylthio-4-propoxyphenyl acetonitrile

→

ethyl 3-methoxy-5-methylthio-4-propoxy-α-cyanobenzeneacetate

収率 92.0%

溶媒

toluene

反応条件

後処理

1. 1
   workup.ADDITIONwas added slowly
2. 2
   温度The mixture was refluxed for 3 hours
3. 3
   その他EtOH was removed under vacuum
4. 4
   ろ過The solid was filtered
5. 5
   洗浄washed with toluene (3×) and ether (3×)
6. 6
   workup.DISSOLUTIONThe solid dissolved
7. 7
   その他a brown oil formed
8. 8
   抽出The oil was extracted with ether (3×)
9. 9
   洗浄the combined ether extracts were washed with H2O (2×), saturated NaCl (2×)
10. 10
    乾燥finally dried over MgSO4
11. 11
    その他The ether was removed under vacuum

実験手順

1.4 g of sodium was dissolved in absolute EtOH with warming to 70° C., then EtOH was removed under vacuum to give a white solid residue of NaOEt. A mixture of 35 ml of diethyl carbonate, 43 ml of toluene, 13.46 g of 3-methoxy-5-methylthio-4-propoxyphenyl acetonitrile was added slowly. The mixture was refluxed for 3 hours. EtOH was removed under vacuum. The solid was filtered and washed with toluene (3×) and ether (3×). The solid was suspended in 200 ml of H2O and acidified with 6N HCl. The solid dissolved and a brown oil formed. The oil was extracted with ether (3×), the combined ether extracts were washed with H2O (2×), saturated NaCl (2×) and finally dried over MgSO4. The ether was removed under vacuum to give 16 g (92% yield) of ethyl 3-methoxy-5-methylthio-4-propoxy-α-cyanobenzeneacetate.

出典