反応 #1256725

反応方程式

methyl 5-propyl-2-trifluoromethanesulfonyloxycyclohex-1-enecarboxylate

4-ethoxy-3-fluoro-2-(2-methoxyethoxymethoxy)benzeneboronic acid

sodium metaborate

hydrazinium hydroxide

→

3-ethoxy-4-fluoro-8-propyl-7,8,9,10-tetrahydrobenzo[c]chromen-6-one

溶媒

water

water

tetrahydrofuran

反応条件

後処理

1. 1
   その他the aqueous phase is separated off
2. 2
   抽出extracted twice with MTB ether
3. 3
   洗浄The combined organic phases are washed with saturated sodium chloride soln
4. 4
   乾燥and dried over sodium sulfate
5. 5
   その他The solvent is removed under reduced pressure
6. 6
   ろ過the residue is filtered through silica gel with n-heptane/MTB ether (6:4)

実験手順

18.2 g (56.6 mmol) of methyl 5-propyl-2-trifluoromethanesulfonyloxycyclohex-1-enecarboxylate, 21.5 g (74.6 mmol) of 4-ethoxy-3-fluoro-2-(2-methoxyethoxymethoxy)benzeneboronic acid, 1.5 ml of water, 33 g (120 mmol) of sodium metaborate, 1.12 g (1.6 mmol) of bis(triphenylphosphine)palladium(II) chloride and 0.1 ml (1.6 mmol) of hydrazinium hydroxide are heated under reflux overnight in 300 ml of tetrahydrofuran. After addition of water, the aqueous phase is separated off and extracted twice with MTB ether. The combined organic phases are washed with saturated sodium chloride soln. and dried over sodium sulfate. The solvent is removed under reduced pressure, and the residue is filtered through silica gel with n-heptane/MTB ether (6:4), giving 3-ethoxy-4-fluoro-8-propyl-7,8,9,10-tetrahydrobenzo[c]chromen-6-one as colourless crystals.

出典