Water → 4-Benzyloxy-2-fluoro-5-methoxy-benzaldehyde

HRID 253416

반응식

HRID 253416 반응식
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[C:7]([O:11][CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C)C=O>[CH2:15]([O:10][C:8]1[C:7]([O:11][CH3:12])=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([F:1])[CH:9]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 5981552-Fluoro-4-hydroxy-5-methoxybenzaldehyde

생성물 1

HCID 5614564-Benzyloxy-2-fluoro-5-methoxy-benzaldehyde

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-Fluoro-4-hydroxy-5-methoxy-benzaldehyde (39, 1.62 g, 9.52 mmol, prepared as described in Scheme 12 of Example 15) was dissolved in N,N-dimethylformamide (50 mL) and sodium hydride (60% dispersion in mineral oil, 530 mg, 13 mmol) was added. After 20 minutes, benzyl bromide (1.5 mL, 12 mmol) was added to the reaction mixture. The reaction was stirred at room temperature under an atmosphere of nitrogen for 5.5 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 0-50% ethyl acetate in hexane to provide compound as a white solid, consistent with the desired structure by 1H-NMR (83, 2.0 g, 81%).

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 0-50% ethyl acetate in hexane
  7. customto provide compound as a white solid

출처 및 근거

ORD 기록
ord-e1916fe71c3f4a51b5df7569e6857a7b
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872018B2

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