Dimethyl 3-oxoglutarate → Methyl 2-(2-methoxy-2-oxoethyl)thiophene-3-carboxylate

HRID 270640

반응식

HRID 270640 반응식
[CH3:1][O:2][C:3]([CH2:5][C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=O)=[O:4].O[CH:14]1[CH2:19]SC(O)C[S:15]1.[Br-].[Li+]>O1CCOCC1>[CH3:1][O:2][C:3]([CH2:5][C:6]1[S:15][CH:14]=[CH:19][C:8]=1[C:9]([O:11][CH3:12])=[O:10])=[O:4]

참가 물질

5

반응물 3

HCID 74591Dimethyl 3-oxoglutarateHCID 82050Lithium BromideHCID 983301,4-Dithiane-2,5-diol

생성물 1

HCID 58952963Methyl 2-(2-methoxy-2-oxoethyl)thiophene-3-carboxylate수율 82.4%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

100.0 g of dimethyl 1,3-acetonedicarboxylate was dissolved in 2,800 ml of dioxane, and added thereto were 52.5 g of 2,5-dihydroxy-1,4-dithiane and 5.0 g of lithium bromide. The resulting mixture was refluxed for 15 hours, cooled to room temperature, and concentrated by evaporation. To the residue, 1,000 ml of n-hexane was added, stirred, and the hexane layer was separated. This extraction procedure was repeated twice using 500 ml portions of n-hexane. The separated n-hexane layers were combined and concentrated under reduced pressure to obtain 60.9 g (yield of 49%) of the title compound as an oil, which was directly used in the next step without any purification. An analytical sample of the title compound could be obtained by vacuum distillation.

후처리

  1. additionadded
  2. temperatureThe resulting mixture was refluxed for 15 hours
  3. concentrationconcentrated by evaporation
  4. additionTo the residue, 1,000 ml of n-hexane was added
  5. customthe hexane layer was separated
  6. extractionThis extraction procedure
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e0ca6cd818a64c73aa1634761220ada2
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449580B2

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