反応 #73499

反応方程式

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

Cs2CO3

NaI

2-dimethylaminoethyl chloride hydrochloride

→

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

溶媒

DCM

CH3CN

反応条件

後処理

1. 1
   ろ過The reaction medium is filtered
2. 2
   濃縮concentrated under reduced pressure
3. 3
   その他The residue obtained
4. 4
   洗浄washed with brine (30 mL)
5. 5
   乾燥dried over Na2SO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated under reduced pressure
8. 8
   その他purified by chromatography on a column of silica gel
9. 9
   洗浄eluting with a DCM/MeOH gradient of 0 to 10% MeOH
10. 10
    濃縮After concentrating under reduced pressure, 409 mg of methyl 2-{3-[2-(dimethylamino)ethoxy]benzyl}-3-oxobutanoate
11. 11
    その他are obtained in the form of a brown wax

実験手順

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.

出典