Реакция #73499

Уравнение реакции

methyl 2-(3-hydroxybenzyl)-3-oxobutanoate

Cs2CO3

NaI

2-dimethylaminoethyl chloride hydrochloride

→

methyl 2-{3-[2-(dimethylamino)ethoxy]benzyl}-3-oxobutanoate

Растворители

DCM

CH3CN

Условия реакции

Обработка

1. 1
   ФильтрацияThe reaction medium is filtered
2. 2
   Концентрированиеconcentrated under reduced pressure
3. 3
   ДругоеThe residue obtained
4. 4
   Промывкаwashed with brine (30 mL)
5. 5
   Сушкаdried over Na2SO4
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated under reduced pressure
8. 8
   Другоеpurified by chromatography on a column of silica gel
9. 9
   Промывкаeluting with a DCM/MeOH gradient of 0 to 10% MeOH
10. 10
    КонцентрированиеAfter concentrating under reduced pressure, 409 mg of methyl 2-{3-[2-(dimethylamino)ethoxy]benzyl}-3-oxobutanoate
11. 11
    Другоеare obtained in the form of a brown wax

Методика

A mixture of 1.5 g (6.75 mmol) of methyl 2-(3-hydroxybenzyl)-3-oxobutanoate, 6.6 g (20.25 mmol) of anhydrous Cs2CO3, 0.1 g (0.67 mmol) of NaI and 1 g (7.1 mmol) of 2-dimethylaminoethyl chloride hydrochloride in 20 mL of anhydrous CH3CN is heated for 4 hours at 90° C., and then stirred overnight at room temperature. The reaction medium is filtered and then concentrated under reduced pressure. The residue obtained is taken up in DCM (100 mL), washed with brine (30 mL), dried over Na2SO4, filtered, concentrated under reduced pressure and then purified by chromatography on a column of silica gel, eluting with a DCM/MeOH gradient of 0 to 10% MeOH. After concentrating under reduced pressure, 409 mg of methyl 2-{3-[2-(dimethylamino)ethoxy]benzyl}-3-oxobutanoate are obtained in the form of a brown wax.

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