反応 #40288

反応方程式

3-hydroxy-1,2,3-benzotriazin-4(3H)-one

Pentynoic acid

dicyclohexylcarbodiimide

3-Hydroxy-1,2,3-benzotriazin-4(3H)-one

→

Pent-4-ynoic Acid 4-oxo-4H-benzo[d][1,2,3]triazin-3-yl Ester

溶媒

THF

THF

反応条件

後処理

1. 1
   温度The solution was cooled in a brine-icewater bath
2. 2
   その他2 h
3. 3
   その他at room temperature
4. 4
   ろ過Precipitated salts were filtered off
5. 5
   濃縮The filtrate was concentrated in vacuo
6. 6
   その他crystallized from hexane (4 mL)
7. 7
   ろ過The crystals were filtered off
8. 8
   その他dried

実験手順

Pentynoic acid (200 mg, 2.04 mmol) was dissolved in THF (4 mL). The solution was cooled in a brine-icewater bath. A solution of dicyclohexylcarbodiimide (421 mg, 2.04 mmol) in THF (2 mL) was added. 3-Hydroxy-1,2,3-benzotriazin-4(3H)-one (333 mg, 2.04 mmol) was added after 5 minutes. The reaction mixture was stirred 1 h at −10° C. and then 2 h at room temperature. TLC indicated full conversion of 3-hydroxy-1,2,3-benzotriazin-4(3H)-one (eluent: ethyl acetate). Precipitated salts were filtered off. The filtrate was concentrated in vacuo and crystallized from hexane (4 mL). The crystals were filtered off and dried. Yield: 450 mg, 93%. RF=0.8 (ethyl acetate).

出典