反応 #417366

反応方程式

6-Formyl-3-propylindole

sodium hydride

methyl 4-bromomethyl-3-methoxybenzoate

→

methyl 3-methoxy-4-(6-formyl-3-propylindol-1-ylmethyl)benzoate

収率 97.6%

溶媒

N,N-dimethylformamide

DMF

DMF

反応条件

後処理

1. 1
   その他The cooling bath was removed
2. 2
   workup.STIRRINGthe mixture stirred for 3.5 hr
3. 3
   workup.ADDITIONpoured into 1N hydrochloric acid (75 ml)
4. 4
   抽出extracted with ethyl acetate (15 ml)
5. 5
   抽出The organic extract
6. 6
   洗浄was washed (water (twice), brine),
7. 7
   乾燥dried (MgSO4)
8. 8
   その他evaporated
9. 9
   その他to give a dark oil
10. 10
    その他The product was purified by flash chromatography
11. 11
    洗浄eluting with 55:40:5 hexane

実験手順

6-Formyl-3-propylindole (1.0 g) in N,N-dimethylformamide (DMF) (10 ml) was added slowly to a stirred suspension of sodium hydride (0.128 g, oil-free) in dry DMF (30 ml) at 0° under an atmosphere of nitrogen. The mixture was stirred at 0° for 60 min and methyl 4-bromomethyl-3-methoxybenzoate (1.38 g) in dry DMF (10 ml) was added dropwise. The cooling bath was removed, the mixture stirred for 3.5 hr, then poured into 1N hydrochloric acid (75 ml), and extracted with ethyl acetate (15 ml). The organic extract was washed (water (twice), brine), dried (MgSO4) and evaporated to give a dark oil. The product was purified by flash chromatography, eluting with 55:40:5 hexane:methylene chloride:ethyl acetate, to give methyl 3-methoxy-4-(6-formyl-3-propylindol-1-ylmethyl)benzoate (1.9 g, 97%) as a yellow oil; partial NMR(250 MHz, DMSO-d6): 0.95(t, 3H, CH2CH3), 1.65(m, 2H, CH2CH3), 2.70(t, 2H, CH2CH2CH3), 3.83(s, 3H, OCH3), 3.95(s, 3H, OCH3), 5.50(s, 2H, NCH2), 9.96(s, 1H, CHO).

出典