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

HRID 333806ノート

反応式

HRID 333806 の反応式
C[O:2][C:3](=O)[CH:4]([C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[Cl:14])[CH3:5].[H-].C([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:14][C:7]1[CH:8]=[CH:9][C:10]([O:12][CH3:13])=[CH:11][C:6]=1[CH:4]([CH3:5])[CH:3]=[O:2]

参加物

6

反応物 4

HCID 887MethanolHCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 574213402-(2-Chloro-5-methoxy-phenyl)-propionic acid methyl ester

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-(2-Chloro-5-methoxy-phenyl)-propionic 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 and then 1N potassium sodium tartrate solution (10 mL). The cooling bath was removed and the mixture was allowed to warm to RT. 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 (710 mg) and was used without further purification. 1H-NMR, (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 RT
  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-ac7c4471d9e94d38a0f007446973b3f0
出典データセット
uspto-grants-2014_11
特許番号
US08883786B2

反応ノート

読み込み中…