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

HRID 253416

反応式

HRID 253416 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-e1916fe71c3f4a51b5df7569e6857a7b
出典データセット
uspto-grants-2011_01
特許番号
US07872018B2

関連ノート

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