تفاعل #77767

معادلة التفاعل

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

المردود 93.7%

المذيبات

piperidine

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwere added
2. 2
   أخرىThe solution was evaporated
3. 3
   أخرىflushed with argon
4. 4
   استخلاصextracted with ether
5. 5
   غسيلThe combined organic phases were washed with water
6. 6
   تجفيفdried over Na2SO4
7. 7
   أخرىPurification by column chromatography with CH2Cl2/MeOH 30:1

الإجراء التجريبي

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+).

المصدر