Acetone → HCID 58674658、化合物

HRID 1994118ノート

反応式

HRID 1994118 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 58674658HCID 58674658、化合物収率 61.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8bd329db5afa40d19095c0ad02d41faf
出典データセット
uspto-grants-2010_01
特許番号
US07652041B2

反応ノート

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