تفاعل #1371527

معادلة التفاعل

methylene chloride

methyl 6-methoxy-1-hydroxy-1,2,3,4-tetrahydro-2-naphthylacetate

hydrogen chloride

1-diethylamino-1,1,2-trifluoro-2-chloroethane

→

methyl 6-methoxy-1-fluoro-1,2,3,4-tetrahydro-2-naphthylacetate

6-methoxy-1,2-dihydro-2-naphthylacetate

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONA mixture of 25 g
2. 2
   أخرىThe fluoroination reaction mixture
3. 3
   workup.ADDITIONis added to 250 ml
4. 4
   أخرىthe resulting mixture is separated
5. 5
   غسيلthe methylene chloride phase is washed with water
6. 6
   تجفيفdried over sodium sulfate
7. 7
   أخرىevaporated

الإجراء التجريبي

A mixture of 25 g. of methyl 6-methoxy-1-hydroxy-1,2,3,4-tetrahydro-2-naphthylacetate, 38 g. of 1-diethylamino-1,1,2-trifluoro-2-chloroethane and 150 ml. of methylene chloride are allowed to stand for 24 hours. The fluoroination reaction mixture is added to 250 ml. of water containing 12 g. of hydrogen chloride; the resulting mixture is separated and the methylene chloride phase is washed with water, dried over sodium sulfate, and evaporated to yield methyl 6-methoxy-1-fluoro-1,2,3,4-tetrahydro-2-naphthylacetate and 6-methoxy-1,2-dihydro-2-naphthylacetate. The mixture is separated on alumina eluting with acetone: diethyl ether (1:4) and the separated fractions are identified by ultraviolet spectroscopy. The fraction containing methyl 6-methoxy-1-fluoro-2-naphthylacetate is evaporated and the residue is refluxed with 23 g. of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and 500 ml. of xylene for six hours. The cooled mixture is filtered and chromatographed on alumina eluting with chloroform. The fraction containing the product is evaporated to yield methyl 6-methoxy-1-fluoro- 2-naphthylacetate.

المصدر