Dichloromethane → HCID 69275389、化合物

HRID 2375382ノート

反応式

HRID 2375382 の反応式
[C:1]([C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][C:11]=2[O:18][CH3:19])[C:5]=1[CH3:20])(=[O:3])[CH3:2].B(Br)(Br)Br.C(Cl)Cl>>[C:1]([C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=2[O:18][CH3:19])[C:5]=1[CH3:20])(=[O:3])[CH3:2]

参加物

4

反応物 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 393723951-[1-(2,4-Dimethoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]ethan-1-one

生成物 1

HCID 69275389HCID 69275389、化合物

実験手順

To a solution of 3-acetyl-1-(2,4-dimethoxyphenyl)-2,5-dimethylpyrrole (2.73 g, 10 mmol) (EXAMPLE 33) in CH2Cl2at rt (75 mL) was added a 1.0M solution of boron tribromide in CH2Cl2 (15 mL, 15 mmol) and the reaction monitored by LC. After complete consumption of the starting material, the reaction was carefully quenched with saturated NaHCO3 and partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered, concentrated in vacuo, and purified by flash chromatography to give 3-acetyl-2,5-dimethyl-1-(4-hydroxy-2-methoxyphenyl)pyrrole as a tan solid: 1H NMR (CDCl3, 500 MHz) δ 6.92 (d, 1H), 6.61 (d, 1H), 6.54 (dd, 1H), 6.32 (s, 1H), 3.72 (s, 3H), 2.44 (s, 3H), 2.26 (s, 3H), 1.93 (s, 3H), 1.69 (br s, 1H); MS (ESI) 260 (M+H)+.

後処理

  1. customAfter complete consumption of the starting material
  2. customthe reaction was carefully quenched with saturated NaHCO3
  3. custompartitioned between EtOAc and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-ee4b61021eb24c619151a261c472286c
出典データセット
uspto-grants-2008_12
特許番号
US07465730B2

反応ノート

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