Sodium hydride → 2-(4-Chlorophenyl)-1-(5'-methyl[2,2'-bithienyl]-5-yl)ethene

HRID 414583

반응식

HRID 414583 반응식
[H-].[Na+].[CH:3]([C:5]1[S:9][C:8]([C:10]2[S:11][C:12]([CH3:15])=[CH:13][CH:14]=2)=[CH:7][CH:6]=1)=O.[Cl:16][C:17]1[CH:31]=[CH:30][C:20]([CH2:21]P(=O)(OCC)OCC)=[CH:19][CH:18]=1>CN(C)C=O>[Cl:16][C:17]1[CH:31]=[CH:30][C:20]([CH:21]=[CH:3][C:5]2[S:9][C:8]([C:10]3[S:11][C:12]([CH3:15])=[CH:13][CH:14]=3)=[CH:7][CH:6]=2)=[CH:19][CH:18]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydride2회HCID 99240Diethyl 4-chlorobenzylphosphonateHCID 49872785-(5-Methylthiophen-2-yl)thiophene-2-carbaldehyde

생성물 1

HCID 543035212-(4-Chlorophenyl)-1-(5'-methyl[2,2'-bithienyl]-5-yl)ethene

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Under a nitrogen atmosphere, 0.12 gram (0.0050 mole) of sodium hydride was added to a stirred solution of 1.2 gram (0.0057 mole) of 5-formyl-5'-methyl[2,2'-bithienyl] and 1.7 gram (0.0064 mole) of diethyl 4-chlorobenzylposphonate in 20 mL of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for about three huurs. Analysis of the reaction mixture by thin layer chromatography indicated starting materials remained. Additional sodium hydride was added, and the mixture was stirred at room temperature for several hours. The reaction mixture was quenched with an aqueous solution saturated with ammonium chloride. This mixture was extracted several times with diethyl ether. The extracts were combined and washed with an aqueous solution saturated with sodium chloride. The washed extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure leaving a residue. This residue was purified by column chromatography on silica gel to yield 2-(4-chlorophenyl)-1-(5'-methyl[2,2'-bithienyl]-5-yl)ethene as a solid, m.p. 157°-162° C.

후처리

  1. stirringthe mixture was stirred at room temperature for several hours
  2. customThe reaction mixture was quenched with an aqueous solution saturated with ammonium chloride
  3. extractionThis mixture was extracted several times with diethyl ether
  4. washwashed with an aqueous solution saturated with sodium chloride
  5. extractionThe washed extract
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated under reduced pressure
  9. customleaving a residue
  10. customThis residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-dd85b256c9904ba0912b9d199ba67bd7
출처 데이터셋
uspto-grants-1988_12
특허 번호
US04792567

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