تفاعل #710679

معادلة التفاعل

sodium hydroxide

2,2,3,3,3-pentafluoropropan-1-ol

sodium hydride

methyl 6-chloronicotinate

→

title compound

المردود 34.0%

methyl 6-(2,2,3,3,3-pentafluoropropoxy)nicotinate

المردود 34.0%

المذيبات

N,N-dimethylacetamide

N,N-dimethylacetamide

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture is stirred for 30 minutes at room temperature
2. 2
   workup.STIRRINGThen, the mixture is stirred at 90° C. for 2 hours
3. 3
   استخلاصThe mixture is extracted with n-hexane/ethyl acetate (1:2, 200 mL)
4. 4
   غسيلThe organic layer is washed with water, brine
5. 5
   تجفيفdried over sodium sulfate
6. 6
   تركيزThe organic solvent is concentrated under reduced pressure
7. 7
   أخرىthe residue is purified by column chromatography on amine gel
8. 8
   غسيلeluting with n-hexane/ethyl acetate (30:1)

الإجراء التجريبي

To a stirred suspension of sodium hydride (3.9 g, 96 mmol, 60% in oil) in N,N-dimethylacetamide (160 mL) is added dropwise 2,2,3,3,3-pentafluoropropan-1-ol (6.4 mL, 64 mmol) at 0° C. After stirring for 10 minutes, a solution of methyl 6-chloronicotinate (5.5 g, 32 mmol) in N,N-dimethylacetamide (10 mL) is added dropwise at 0° C., and the mixture is stirred for 30 minutes at room temperature. Then, the mixture is stirred at 90° C. for 2 hours. After cooled to room temperature, 2M aqueous sodium hydroxide is added (pH is around 6). The mixture is extracted with n-hexane/ethyl acetate (1:2, 200 mL). The organic layer is washed with water, brine, and dried over sodium sulfate. The organic solvent is concentrated under reduced pressure, and the residue is purified by column chromatography on amine gel eluting with n-hexane/ethyl acetate (30:1) to give 3.1 g (34% yield) of the title compound as brown oil. MS (ESI) m/z: 286 (M+H)+.

المصدر