반응 #2487404

반응 방정식

2,3,4,5,6-Pentafluorophenol

triethylamine

Cyclobut-1-enecarboxylic acid

oxalyl dichloride

cyclobut-1-enecarboxylic chloride

→

13

수율 44.0%

Perfluorophenyl cyclobut-1-enecarboxylate

수율 44.0%

용매

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   온도The temperature of the solution was raised to room temperature
2. 2
   기타to react for 1 h
3. 3
   기타The solvent was evaporated
4. 4
   workup.ADDITIONbefore being added to
5. 5
   workup.STIRRINGThe reaction mixture was stirred for 16 h at rt
6. 6
   기타The reaction was quenched with 1 N HCl
7. 7
   추출was extracted with CH2Cl2 (30 ml)
8. 8
   세척The CH2Cl2 solution was washed with 5% NaHCO3 (2×10 ml)
9. 9
   건조dried over Na2SO4
10. 10
    농축concentrated by rotary evaporation
11. 11
    기타purified by flash column chromatography (100% CH2Cl2)

실험 절차

Cyclobut-1-enecarboxylic acid (0.51 mmol, 50 mg) was dissolved in 0.5 ml dry CH2Cl2. The solution was cooled to 0° C. and oxalyl dichloride (0.51 mmol, 43 μl) was added. The temperature of the solution was raised to room temperature, and the mixture was allowed to react for 1 h. The solvent was evaporated to generate a viscous oil. 2,3,4,5,6-Pentafluorophenol (0.51 mmol, 94 mg) and triethylamine (1.02 mmol, 142 μl) were dissolved in 0.5 ml dry CH2Cl2, and the solution was stirred at 0° C. for 45 min before being added to a vial containing cyclobut-1-enecarboxylic chloride. The reaction mixture was stirred for 16 h at rt. The reaction was quenched with 1 N HCl, and was extracted with CH2Cl2 (30 ml). The CH2Cl2 solution was washed with 5% NaHCO3 (2×10 ml), dried over Na2SO4, concentrated by rotary evaporation, and then purified by flash column chromatography (100% CH2Cl2) to yield 13 as a colorless oil (59 mg, 44%). 1H-NMR (500 MHz, CDCl3) δ 7.12 (s, 1H), 2.86 (m, 2H), 2.60 (m, 2H). 13C-NMR (125 MHz, CDCl3) δ 156.7, 152.6, 142.1, 140.3, 138.8, 138.3, 135.2, 53.3, 30.6, 29.2. HRMS (ESI) calcd. for C11H6O2F5 [M+H]+ 265.0293, found 265.0288.

출처