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Toluene → HCID 89649425, 화합물

HRID 2207653
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HRID 2207653 반응식
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([F:23])=[C:8]([C:10]2[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[N:13]=[C:12]([C:19](OC)=[O:20])[CH:11]=2)[CH:9]=1)[CH3:2].CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1>C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([F:23])=[C:8]([C:10]2[CH:15]=[C:14]([CH:16]([CH3:17])[CH3:18])[N:13]=[C:12]([CH:19]=[O:20])[CH:11]=2)[CH:9]=1)[CH3:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 89649130HCID 89649130, 화합물

생성물 1

HCID 89649425HCID 89649425, 화합물수율 87.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

A solution of methyl 4-(5-ethoxy-2-fluoro-phenyl)-6-isopropyl-pyridine-2-carboxylate (which may be prepared as described in Description 115) (0.72 g, 2.27 mmol) in THF (20 mL) was cooled to −78° C. under nitrogen and was treated dropwise with 1M DIBAL in toluene (4.54 mL, 4.54 mmol) over 10 minutes. The mixture was stirred at −78° C. for 2 hrs. The mixture was quenched with satd. aq. NH4Cl solution (5 ml) and the mixture was allowed to reach room temperature and stirred for 30 mins. Celite was added to the mixture and the mixture was stirred for 10 minutes and then filtered through Celite and concentrated to give 4-(5-ethoxy-2-fluoro-phenyl)-6-isopropyl-pyridine-2-carbaldehyde (D116) (0.57 g);

후처리

  1. customThe mixture was quenched with satd
  2. customto reach room temperature
  3. stirringstirred for 30 mins
  4. additionCelite was added to the mixture
  5. stirringthe mixture was stirred for 10 minutes
  6. filtrationfiltered through Celite
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4b040b9a37c84d7d8dcbff9529ec0577
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09376436B2

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