반응 #85483

반응 방정식

5-(tetradecyloxy)furan-2-carboxylic acid

EtOAc

N,N′-dicyclohexylcarbodiimide

2,2,2-trifluoroethanol

→

title compound

수율 70.0%

2,2,2-trifluoroethyl 5-(tetradecyloxy)furan-2-carboxylate

수율 70.0%

용매

CH2Cl2

—

Hexanes

반응 조건

후처리

1. 1
   기타The flask was capped
2. 2
   기타consumption of the starting material
3. 3
   workup.ADDITIONThe resulting suspension was diluted with CH2Cl2 (40 mL)
4. 4
   여과filtered
5. 5
   농축concentrated
6. 6
   기타This crude material was purified by flash chromatography
7. 7
   세척eluting with 5-20% EtOAc in Hexanes
8. 8
   기타The resulting solid was further purified by recrystallization in 30 mL of hot 2-propanol with the addition of a minimum amount of water

실험 절차

To a stirred, room temperature suspension of 5-(tetradecyloxy)furan-2-carboxylic acid (1.3 g, 4.0 mmol) in CH2Cl2 (40 mL) was added N,N′-dicyclohexylcarbodiimide (0.990 g, 4.8 mmol), N,N-dimethylaminopyridine (0.488 g, 4.0 mmol) and 2,2,2-trifluoroethanol (0.875 mL, 12.0 mmol). The flask was capped and stirring was continued for 16 hrs at which time TLC (10% EtOAc in Hexanes Rf=0.05 (SM) and 0.25 (Prod)) indicated complete consumption of the starting material. The resulting suspension was diluted with CH2Cl2 (40 mL), filtered and concentrated. This crude material was purified by flash chromatography eluting with 5-20% EtOAc in Hexanes. The resulting solid was further purified by recrystallization in 30 mL of hot 2-propanol with the addition of a minimum amount of water to yield 1.13 g (70%) of the title compound as white needles. MS (m/z, ES−): 406.0 (M−1, 100%); EA found for C23H36F3NO2: C, 62.20; H, 8.18; calcd: C, 62.05; H, 8.18; 1H NMR (400 MHz, DMSO-d6) δ: 7.4 (d, 1H), 5.7 (d, 1H), 4.9 (q, 2H), 4.2 (t, 2H), 1.50-1.57 (m, 2H), 1.10-1.20 (m, 22H), 0.85 (t, 3H).

출처