반응 #653417

반응 방정식

3,4-dimethoxyphenylacetic acid

chloroform

chloroform

→

(3,4-dimethoxyphenyl)acetyl chloride

반응 조건

후처리

1. 1
   기타to give a brown oil which
2. 2
   기타The reaction mixture is partitioned between 1M sodium hydroxide solution (100 mL) and dichloromethane (80 mL)
3. 3
   기타The organic layer is separated
4. 4
   세척the aqueous is washed with more dichloromethane (2×50 mL)
5. 5
   건조The combined dichloromethane extracts are dried over sodium sulfate
6. 6
   기타the solvent is removed
7. 7
   기타to leave the crude free ester

실험 절차

(3,4-dimethoxyphenyl)acetyl chloride is prepared according to the method described in Example 8 using 3,4-dimethoxyphenylacetic acid (2.85 g, 14.5 mmol) to give a brown oil which is dissolved in chloroform (10 mL). This solution is refluxed for 3 hours with a solution of (±)-trans-[2-(4-morpholinyl)]cyclohexanethiol (2.8 g, 14 mmol) in chloroform (10 mL) under nitrogen. The reaction mixture is partitioned between 1M sodium hydroxide solution (100 mL) and dichloromethane (80 mL). The organic layer is separated and the aqueous is washed with more dichloromethane (2×50 mL). The combined dichloromethane extracts are dried over sodium sulfate, and the solvent is removed to leave the crude free ester. This is purified by column chromatography and converted to the hydrochloride salt by treatment with HCl in ether. The product is recrystallised from hot ethyl acetate/methanol to yield the title compound.

출처