تفاعل #1256725

معادلة التفاعل

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

المذيبات

water

water

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىthe aqueous phase is separated off
2. 2
   استخلاصextracted twice with MTB ether
3. 3
   غسيلThe combined organic phases are washed with saturated sodium chloride soln
4. 4
   تجفيفand dried over sodium sulfate
5. 5
   أخرىThe solvent is removed under reduced pressure
6. 6
   ترشيحthe residue is filtered through silica gel with n-heptane/MTB ether (6:4)

الإجراء التجريبي

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.

المصدر