Réaction #85483

Équation de réaction

5-(tetradecyloxy)furan-2-carboxylic acid

EtOAc

N,N′-dicyclohexylcarbodiimide

2,2,2-trifluoroethanol

→

title compound

Rendement 70.0%

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

Rendement 70.0%

Solvants

CH2Cl2

—

Hexanes

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source