تفاعل #710683

معادلة التفاعل

sodium hydroxide

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

sodium hydride

methyl 6-chloronicotinate

→

title compound

المردود 71.8%

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

المردود 71.8%

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

الإجراء التجريبي

To a stirred suspension of sodium hydride (4.9 g, 120 mmol, 60% in oil) in N,N-dimethylacetamide (100 mL) is added dropwise 2,2,3,3,3-pentafluoropropan-1-ol (8.1 mL, 82 mmol) at 0° C. After stirring for 10 minutes, a solution of methyl 6-chloronicotinate (7.0 g, 41 mmol) in N,N-dimethylacetamide (120 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 to give 8.4 g of the title compound as a crude product (include 2,2,3,3,3-pentafluoropropyl 6-(2,2,3,3,3-pentafluoropropoxy)nicotinate as a byproduct). The residue is used for the next reaction (Step-2) without further purification.

المصدر