Diisobutylaluminum hydride → 3-(4-Methoxyphenyl)propanal

HRID 333913노트

반응식

HRID 333913 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11](O)=[O:12])=[CH:5][CH:4]=1.CC(C[AlH]CC(C)C)C.[NH4+].[Cl-]>C1(C)C=CC=CC=1.C(=O)=O.CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]=[O:12])=[CH:5][CH:4]=1

참가 물질

6

반응물 3

HCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 957503-(p-Methoxyphenyl)propionic acid

생성물 1

HCID 111266073-(4-Methoxyphenyl)propanal수율 70.7%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 18522661Acetone cardice용매

반응 조건

온도
-78 °C

실험 절차

3-(4-Methoxy-phenyl)-propionic acid (9a, 1.80 g, 10.0 mmol) in toluene (25.0 mL) was cooled to −78° C. in dry ice-acetone bath for 5-10 minutes under N2. DIBAL-H (11.0 mmol) was slowly added by syringe and stirred for 2 hours at −78° C. Then, the reaction mixture was poured quickly into an aqueous NH4Cl solution with vigorous stirring. The solution was extracted twice with ether and the organic layer was washed with brine, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to provide 3-(4-methoxy-phenyl)-propionaldehyde (9b, 1.16 g, 7.07 mmol) as yellow oil in 70.7% yield.

후처리

  1. extractionThe solution was extracted twice with ether
  2. washthe organic layer was washed with brine
  3. dry with materialdried over MgSO4(s)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-8b93349babcb42c493cc05b58688e64b
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883793B2

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