反応 #77767

反応方程式

6-Trifluoromethanesulfonyloxy-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

HCl

4-pentynol

4-pentynol

→

6-(5-Hydroxy-pent-1-ynyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

収率 93.7%

溶媒

piperidine

反応条件

後処理

1. 1
   workup.ADDITIONwere added
2. 2
   その他The solution was evaporated
3. 3
   その他flushed with argon
4. 4
   抽出extracted with ether
5. 5
   洗浄The combined organic phases were washed with water
6. 6
   乾燥dried over Na2SO4
7. 7
   その他Purification by column chromatography with CH2Cl2/MeOH 30:1

実験手順

To 850 mg (2.2 mmol) 6-Trifluoromethanesulfonyloxy-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester in 5 ml piperidine, 128.0 mg (0.1 mmol) tetrakis(triphenylphosphine)palladium followed by 21.0 mg (0.1 mmol) copper iodide were added. The solution was evaporated and flushed with argon prior to the addition of 210 μl (2.2 mmol) 4-pentynol at 80° C. over a period of 45 min. Further 0.2 ml (2.1 mmol) 4-pentynol were added and the solution was stirred for 2 h. The mixture was added to ice water, acidified with 2M HCl and extracted with ether. The combined organic phases were washed with water and dried over Na2SO4. Purification by column chromatography with CH2Cl2/MeOH 30:1 yielded 650 mg (92%) 6-(5-Hydroxy-pent-1-ynyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester as light brown oil, MS: 316 (MH+).

出典