Methanol → 2-(2-Chloro-5-methoxy-phenyl)-propionaldehyde

HRID 1095948ノート

反応式

HRID 1095948 の反応式
CO[C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[Cl:13].[H-].[CH2:16]([Al+]CC(C)C)C(C)C.CO.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[Cl:13][C:6]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=1[CH:4]([CH3:16])[CH:3]=[O:14]

参加物

6

反応物 4

HCID 887MethanolHCID 9855836Potassium sodium tartarateHCID 15576550Methyl 2-(2-chloro-5-methoxyphenyl)acetateHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 574499712-(2-Chloro-5-methoxy-phenyl)-propionaldehyde

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
-78 °C

実験手順

2-Chloro-5-methoxy-benzeneacetic acid methyl ester (850 mg) was dissolved in toluene (40 mL) and cooled to −78° C. Diisobutylaluminium hydride (20% in toluene, 3.69 mL) was added over a period of 15 minutes. Stirring was continued for 45 minutes at −78° C. Methanol (2 mL) was added followed by 1M potassium sodium tartrate solution (10 mL). The cooling bath was removed and the mixture was allowed to warm to r.t. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and evaporated. The title compound was obtained as a light yellow oil (710mg, 96%) and was used without further purification. 1H-NMR (δ, CDCl3): 9.72 (s, 1H), 7.34 (d, 1H), 6.79 (dd, 1H), 6.66 (d, 1H), 4.10 (q, 1H), 3.79 (s, 3H), 1.43 (d, 3H).

後処理

  1. customThe cooling bath was removed
  2. temperatureto warm to r.t
  3. additionThe mixture was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated

出典と根拠

ORDレコード
ord-1246e4b3d1ac42e99aafe7f1c3f03c5e
出典データセット
uspto-grants-2012_03
特許番号
US08138189B2

反応ノート

読み込み中…