反応 #85483

反応方程式

5-(tetradecyloxy)furan-2-carboxylic acid

EtOAc

N,N′-dicyclohexylcarbodiimide

2,2,2-trifluoroethanol

→

title compound

収率 70.0%

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

収率 70.0%

溶媒

CH2Cl2

—

Hexanes

反応条件

後処理

1. 1
   その他The flask was capped
2. 2
   その他consumption of the starting material
3. 3
   workup.ADDITIONThe resulting suspension was diluted with CH2Cl2 (40 mL)
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他This crude material was purified by flash chromatography
7. 7
   洗浄eluting with 5-20% EtOAc in Hexanes
8. 8
   その他The resulting solid was further purified by recrystallization in 30 mL of hot 2-propanol with the addition of a minimum amount of water

実験手順

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).

出典