تفاعل #52296

معادلة التفاعل

triethylamine

Triflic anhydride

triphenylphosphine oxide

3-naphthalen-2-yl-3-oxo-propionic acid ethyl ester

→

naphthalene-2-yl-propynoic acid ethyl ester

المردود 42.7%

المذيبات

1,2-dichloroethane

1,2-dichloroethane

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAfter the addition
2. 2
   درجة الحرارةthe reaction mixture was heated
3. 3
   درجة الحرارةat reflux for 1 hr
4. 4
   غسيلwashed with water
5. 5
   تجفيفdried (MgSO4)
6. 6
   أخرىThe solvent was removed under reduced pressure
7. 7
   أخرىthe product was purified via column chromatography with silica eluting with hexane/ethyl acetate (9/1)

الإجراء التجريبي

Triflic anhydride (2.9 mL, 17 mmol) was added dropwise to a solution of triphenylphosphine oxide (4.8 g, 17 mmol) in 1,2-dichloroethane (40 mL) at 0° C. The resulting suspension was stirred for 15 minutes, followed by the dropwise addition of a solution of 3-naphthalen-2-yl-3-oxo-propionic acid ethyl ester (3.2 g, 12 mmol) in 1,2-dichloroethane (40 mL). After the addition was complete, triethylamine (4.0 mL, 29 mmol) was added and the reaction mixture was heated at reflux for 1 hr. The solution was cooled to room temperature, washed with water, and dried (MgSO4). The solvent was removed under reduced pressure, and the product was purified via column chromatography with silica eluting with hexane/ethyl acetate (9/1) to yield naphthalene-2-yl-propynoic acid ethyl ester (1.15 g, 37% yield) as a yellow oil. 1H NMR (CDCl3) δ 8.25 (s, 1H), 7.95 (m, 3H), 7.66 (m, 3H), 4.46 (m, 2H), 1.51 (t, 3H, J=8.0 Hz).

المصدر