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

HRID 333806노트

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HRID 333806 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ac7c4471d9e94d38a0f007446973b3f0
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883786B2

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