Hydrochloric Acid → HCID 54350709, 화합물

HRID 443994

반응식

HRID 443994 반응식
[C:1]([O:10][CH:11]([CH3:13])[CH3:12])(=[O:9])[CH2:2][C:3]([O:5][CH:6]([CH3:8])[CH3:7])=[O:4].[H-].[Na+].[H][H].I[C:19]1[CH:23]=[CH:22][S:21][CH:20]=1.Cl>N1C2C(=CC=CC=2)C=CC=1.[Cu]Br.C1(C)C=CC=CC=1.O>[S:21]1[CH:22]=[CH:23][C:19]([CH:2]([C:3]([O:5][CH:6]([CH3:7])[CH3:8])=[O:4])[C:1]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])=[CH:20]1

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 663323-IodothiopheneHCID 83223Diisopropyl malonateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 54350709HCID 54350709, 화합물

시약·촉매·용매 4

HCID 24593copper(I) bromide촉매HCID 962Water용매HCID 1140Toluene용매HCID 7047Quinoline용매

실험 절차

In the way described before 18.8 g (=0.10 mole) di-isopropyl malonate were mono-deprotonated with 0.10 mole NaH in 112.5 ml quinoline. After the liberation of hydrogen gas had been ceased 16.8 g (=0.080 mole) 3-iodothiophene and 11.5 g (=0.080 mole) copper (I) bromide were added. The resultant mixture was stirred under N2 atmosphere at a temperature of 100° C. during a period of 5 hours and subsequently poured out into an icy-cold mixture of 112 ml water and 112 ml concentrated HCl. The precipitated copper salts were collected on a Buchner funnel and washed with chloroform. The filtrate was extracted with chloroform too. The two chloroform layers were joined and dried over magnesium sulphate. After removal of the solvent a residue remained which according to GLC analysis contained 0.44 g 3-iodothiophene and 12 g di-isopropyl 3-thienylmalonate (=0.044 mole or 55% calculated to the 3-iodothiophene started from). A pure sample was obtained by chromatography over a column filled with silica gel using toluene as elution agent. The product so obtained could be crystallized at -18° C. from petroleum ether 40-60; at room temperature, however, it is a liquid. Identification of the purified product occurred through NMR and IR spectroscopy.

후처리

  1. additionwere added
  2. customThe precipitated copper salts were collected on a Buchner funnel
  3. washwashed with chloroform
  4. extractionThe filtrate was extracted with chloroform too
  5. dry with materialdried over magnesium sulphate
  6. customAfter removal of the solvent a residue
  7. customA pure sample was obtained by chromatography over a column
  8. additionfilled with silica gel
  9. washas elution agent
  10. customThe product so obtained could
  11. custombe crystallized at -18° C. from petroleum ether 40-60
  12. customat room temperature

출처 및 근거

ORD 기록
ord-e122742a273e4fe4b9fc523881f4bbc8
출처 데이터셋
uspto-grants-1981_04
특허 번호
US04262129

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