反応 #79729

反応方程式

cyclohexylmethylbromide

5-carbomethoxy-1,2-dihydro-9H-carbazol-4(3H)-one

H2O

K2CO3

cyclohexylmethyl bromide

→

9-[(cyclohexyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one

収率 97.6%

溶媒

DMF

反応条件

後処理

1. 1
   温度the resulting mixture was heated at 60° C. for 3 hours
2. 2
   抽出extracted with EtOAc (2×25 mL)
3. 3
   洗浄The combined organic layers were washed with H2O (4×50 mL)
4. 4
   乾燥dried over anhydrous Na2SO4
5. 5
   ろ過filtered
6. 6
   濃縮concentrated in vacuo
7. 7
   その他The residue was purified by radial chromatography on silica gel (
8. 8
   洗浄elution with a gradient of 20% to 40% EtOAc/hexanes)

実験手順

A 0° C. suspension of 5-carbomethoxy-1,2-dihydro-9H-carbazol-4(3H)-one (1.0 g, 4.11 mmol), a catalytic amount of NaI (ca. 10 mg) and K2CO3 (1.1 g, 8.22 mmol) in 10 mL of DMF was treated with cyclohexylmethyl bromide (0.631 mL, 4.52 mmol). After stirring overnight at ambient temperature, an additional 0.63 mL cyclohexylmethylbromide was added, and the resulting mixture was heated at 60° C. for 3 hours. The mixture was poured into H2O (30 mL) and extracted with EtOAc (2×25 mL). The combined organic layers were washed with H2O (4×50 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by radial chromatography on silica gel (elution with a gradient of 20% to 40% EtOAc/hexanes) to afford 1.36 g (4.01 mmol; 97%) of 9-[(cyclohexyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one as a white foam. IR (CHCl3, cm−1) 3011, 2932, 2857, 1725, 1649, 1469, 1446, 1288 and 1120. MS (ES) m/e 340 (M+1), 453 (M+AcO−). FAB HRMS m/e, Calcd for C21H26NO3: 340.1913. Found: 340.1916 (M+1).

出典