Triethylamine → (E)-3-(3-methoxyphenyl)acrylic azide

HRID 1852234ノート

反応式

HRID 1852234 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:9]=[CH:10]/[C:11]([OH:13])=O)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.C1C=CC(P([N:35]=[N+:36]=[N-:37])(C2C=CC=CC=2)=O)=CC=1>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:9]=[CH:10]/[C:11]([N:35]=[N+:36]=[N-:37])=[O:13])[CH:6]=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 6376683-Methoxycinnamic Acid

生成物 1

HCID 49782297(E)-3-(3-methoxyphenyl)acrylic azide収率 88%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

To a solution of (E)-3-(3-methoxyphenyl)acrylic acid (15 g, 84 mmol) in benzene (100 ml) was added triethylamine (11.73 ml, 84 mmol) followed by DPPA (23.17 g, 84 mmol) at room temperature. The reaction mass was stirred at the same temperature for 18 h. The solvent was evaporated under reduced pressure and the residue was diluted with water followed by extraction with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to get crude compound. The crude compound was purified by conventional column chromatography (Silica gel, 60-120 mesh) using 10% ethyl acetate in pet ether as mobile phase to get the desire compound as white solid (15 g, 88%). 1H NMR (400 MHz, CDCl3): δ ppm 7.75-7.70 (d, J=20 Hz, 1H), 7.36-6.97 (m, 4H), 6.45-6.40 (d, J=20 Hz, 1H), 3.85 (s, 3H).

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionfollowed by extraction with dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto get crude compound
  8. customThe crude compound was purified by conventional column chromatography (Silica gel, 60-120 mesh)

出典と根拠

ORDレコード
ord-67d88bbc31b3457d907fe0986173ce53
出典データセット
uspto-grants-2015_02
特許番号
US08957203B2

反応ノート

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