反応 #306170

反応方程式

THF

THF

NaOMe

tridecane

hydrogen

THF

THF

THF

→

methyl benzoate

反応条件

後処理

1. 1
   workup.ADDITIONwere successively added to the autoclave
2. 2
   その他placed in a thermostatted oil bath
3. 3
   その他set at 60° C
4. 4
   その他After the mentioned time, the autoclave was removed from the oil bath
5. 5
   温度cooled in a cold-water bath
6. 6
   workup.ADDITIONdiluted with MTBE (5 ml)
7. 7
   洗浄washed with aq. sat. NH4Cl (5 ml)
8. 8
   ろ過filtered over a plug of celite

実験手順

Under argon, a Keim autoclave was charged with [RuCl2(R-BINAP)(dmf)2] (0.01 mmol, 0.05 mol %) and S,S-DPEN (0.01 mmol, 0.05 mol %) followed by THF (2 ml) and the solution stirred for 5 minutes. Then a solution of the desired ester (20 mmol) in THF (2 ml), followed by more THF (2×1 ml), and a solution of tridecane (1 mmol) in THF (2 ml), as internal standard, followed by more THF (2×1 ml), were successively added to the autoclave. Finally, solid NaOMe (1 mmol, 5 mol %) was added and the autoclave was pressurised with hydrogen gas at 50 bars and placed in a thermostatted oil bath set at 60° C. After the mentioned time, the autoclave was removed from the oil bath, and cooled in a cold-water bath. Then, an aliquot (0.4 ml) was taken, diluted with MTBE (5 ml), washed with aq. sat. NH4Cl (5 ml), and filtered over a plug of celite and analyzed by GC.

出典