Acetone → HCID 58674658, 화합물

HRID 1994118노트

반응식

HRID 1994118 반응식
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]2[CH3:14])[CH:5]=[CH:6][CH:7]=1.[Li]CCCC.[CH3:20][C:21]([CH3:23])=[O:22]>C1COCC1>[CH3:14][C:9]1[N:8]([C:4]2[CH:3]=[C:2]([C:21]([OH:22])([CH3:23])[CH3:20])[CH:7]=[CH:6][CH:5]=2)[C:12]([CH3:13])=[CH:11][CH:10]=1

참가 물질

5

반응물 3

HCID 180AcetoneHCID 47636541-(3-bromophenyl)-2,5-dimethyl-1H-pyrroleHCID 178418339Butyllithium

생성물 1

HCID 58674658HCID 58674658, 화합물수율 61.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 1-(3-bromophenyl)-2,5-dimethyl-1H-pyrrole (1.50 g, 6.00 mmol) in THF (25 mL) was cooled to −78° C. under an atmosphere of argon. To this solution was added n-BuLi (2.50 M in hexane, 2.76 mL, 6.90 mmol) dropwise via syringe. After 30 min, acetone (0.572 mL, 7.8 mmol) was added to the cold solution dropwise via syringe. After 10 min, the cold bath was removed and the reaction mixture was allowed to warm to rt. After 5.5 h, the reaction was quenched by the addition of water. The mixture was extracted with EtOAc and the organic solutions dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography to give the desired product (0.84 g, 61%). LCMS: (FA) ES+ 230.1 (M+1).

후처리

  1. waitAfter 10 min
  2. customthe cold bath was removed
  3. waitAfter 5.5 h
  4. customthe reaction was quenched by the addition of water
  5. extractionThe mixture was extracted with EtOAc
  6. dry with materialthe organic solutions dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-8bd329db5afa40d19095c0ad02d41faf
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652041B2

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