Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → (E)-methyl 3-[3-(methylcarbamoyl)phenyl]prop-2-enoate

HRID 16912

反応式

HRID 16912 の反応式
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([NH:8][CH3:9])=[O:7])=O.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:20][C:21]([O:23][CH3:24])=[O:22])C=CC=CC=1>ClCCl>[CH3:9][NH:8][C:6]([C:5]1[CH:4]=[C:3](/[CH:1]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])[CH:12]=[CH:11][CH:10]=1)=[O:7]

参加物

4

反応物 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 220514333-formyl-N-methylbenzamide

生成物 1

HCID 66589796(E)-methyl 3-[3-(methylcarbamoyl)phenyl]prop-2-enoate収率 97%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 3-formyl-N-methylbenzamide (2.9 g, 17.77 mmol) and methyl 2-triphenylphosphoranylideneacetate (8.91 g, 26.66 mmol) in dichloromethane (85 mL), was stirred at room temperature for 18 h. The reaction mixture was evaporated to dryness. The crude product was purified by silica column chromatography, eluting with a gradient of 0 to 10% MeOH in DCM. Pure fractions were evaporated to dryness to afford impure product. Re-purified by silica column chromatography, eluting with a gradient of 50 to 100% EtOAc in hexanes. Pure fractions were evaporated to dryness to afford (E)-methyl 3-[3-(methylcarbamoyl)phenyl]prop-2-enoate (3.77 g, 97%).

後処理

  1. customThe reaction mixture was evaporated to dryness
  2. customThe crude product was purified by silica column chromatography
  3. washeluting with a gradient of 0 to 10% MeOH in DCM
  4. customPure fractions were evaporated to dryness
  5. customto afford impure product
  6. washRe-purified by silica column chromatography, eluting with a gradient of 50 to 100% EtOAc in hexanes
  7. customPure fractions were evaporated to dryness

出典と根拠

ORDレコード
ord-24af0df68b554f1aa00326ca1f29ca6d
出典データセット
uspto-grants-2010_06
特許番号
US07737149B2

関連ノート

読み込み中…