反応 #339948

反応方程式

LDA

indanone

methyl-4-bromobenzoate

→

title compound 271

収率 17.0%

Methyl 4-(1-oxo-indan-2-ylmethyl)-benzoate

収率 17.0%

溶媒

THF

THF

反応条件

後処理

1. 1
   温度The reaction was then cooled to −78° C.
2. 2
   温度The solution was slowly warmed to −20° C.
3. 3
   workup.STIRRINGstirred during 4 hours
4. 4
   その他The reaction mixture was quenched with HCL 1M
5. 5
   その他the solvent was evaporated
6. 6
   workup.ADDITIONThe residue was diluted in ethyl acetate
7. 7
   洗浄washed with brine
8. 8
   乾燥dried over anhydrous MgSO4
9. 9
   ろ過filtered
10. 10
    濃縮concentrated
11. 11
    その他The crude residue was then purified by flash chromatography on silica gel (5-20% AcOEt/HEx)

実験手順

A 2M LDA solution in THF (4.16 ml, 8.32 mmol) was added to a solution of indanone (1.00 g, 7.57 mmol) in THF (10 ml) at −60° C. The solution was slowly warmed to 0° C. during a period of 15 min. and was agitated for 15 more min. The reaction was then cooled to −78° C. and a solution of methyl-4-bromobenzoate (1.73 g, 7.57 mmol) was slowly added. The solution was slowly warmed to −20° C. and stirred during 4 hours. The reaction mixture was quenched with HCL 1M and the solvent was evaporated. The residue was diluted in ethyl acetate, washed with brine, dried over anhydrous MgSO4, filtered and concentrated. The crude residue was then purified by flash chromatography on silica gel (5-20% AcOEt/HEx) to afford the title compound 271 (245 mg, 17%) as a white solid. LRMS: 280.1 (Calc.); 281.1 (found).

出典