Hydrochloric Acid → Dimethyl 3-thienylmalonate

HRID 443993

반응식

HRID 443993 반응식
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].I[C:13]1[CH:17]=[CH:16][S:15][CH:14]=1.Cl>N1C2C(=CC=CC=2)C=CC=1.[Cu]Br.O>[S:15]1[CH:16]=[CH:17][C:13]([CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[CH:14]1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 663323-Iodothiophene

생성물 1

HCID 12509453Dimethyl 3-thienylmalonate

시약·촉매·용매 3

HCID 24593copper(I) bromide촉매HCID 962Water용매HCID 7047Quinoline용매

반응 조건

온도
80 °C

실험 절차

In the way described before 5.3 g (=0.040 mole) dimethyl malonate were mono-deprotonated with 0.040 mole NaH in 75 ml quinoline. Then 6.7 g (=0.032 mole) 3-iodothiophene and 4.6 g (=0.032 mole) copper (I) bromide were added. The resulting mixture was stirred under N2 atmosphere during a period of 4.5 hours at a temperature of 80° C. and then poured out into a mixture of 75 ml water and 75 ml concentrated HCl. The precipitated copper salts were collected on a Buchner funnel and washed with chloroform. Extraction of the filtrate occured likewise with chloroform. Both chloroform layers were joined and dried over magnesium sulphate. After removal of the solvent 11.0 g of an oily product remained in which by GLC analysis the presence was demonstrated of 1.93 g 3-iodothiophene and 1.32 g di-methyl 3-thienylmalonate (=0.006 mole or 19% calculated to the 3-iodothiophene started from). The product was identified in the same way as described in Example 5.

후처리

  1. customThe precipitated copper salts were collected on a Buchner funnel
  2. washwashed with chloroform
  3. extractionExtraction of the filtrate
  4. dry with materialdried over magnesium sulphate
  5. customAfter removal of the solvent 11.0 g of an oily product

출처 및 근거

ORD 기록
ord-2bddfd2d3a2d4d7e9c8642a7b0b6c7b8
출처 데이터셋
uspto-grants-1981_04
특허 번호
US04262129

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