tert-Butyl acetate → tert-butyl 3-bromo-4-chloro-5-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-2-carboxylate

HRID 1948379노트

반응식

HRID 1948379 반응식
[Br:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[N:4]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])C=1C(OCC)=O.[C:22]([O:26][C:27](=[O:29])[CH3:28])([CH3:25])([CH3:24])[CH3:23].CC(C)([O-])C.[K+]>>[Br:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[N:4]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:14])([CH3:16])[CH3:15])[C:28]=1[C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:29]

참가 물질

4

반응물 3

HCID 10908tert-Butyl acetate2회HCID 23665647Potassium tert-butoxide2회HCID 68515032Ethyl 3-bromo-4-chloro-5-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-2-carboxylate2회

생성물 1

HCID 59406885tert-butyl 3-bromo-4-chloro-5-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-2-carboxylate수율 80.4%

실험 절차

Ethyl 3-bromo-4-chloro-5-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-2-carboxylate (Intermediate 266, 564 mg, 1.42 mmol), t-Butylacetate (330 mg, 2.84 mmol) and potassium t-butoxide (0.14 mmol) were mixed together and stirred at room temperature for 10 minutes, concentrated to an oil under vacuum. t-Butylacetate (330 mg, 2.84 mmol) and potassium t-butoxide (0.14 mmol) were added again into the reaction mixture, repeated the same procedure again. The resulting reaction crude was filtered through a short pass silica gel, washed with ethyl acetate, the combined filtrate was concentrated to an oil and purified by column chromatography (2% ethyl acetate in hexanses) to give the desired product as an oil (485 mg).

후처리

  1. concentrationconcentrated to an oil under vacuum
  2. customThe resulting reaction crude
  3. filtrationwas filtered through a short pass silica gel
  4. washwashed with ethyl acetate
  5. concentrationthe combined filtrate was concentrated to an oil
  6. custompurified by column chromatography (2% ethyl acetate in hexanses)

출처 및 근거

ORD 기록
ord-0996c6e358624c2c8e1eb14fa9c436cd
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399489B2

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