Pyridine → 3,5-Bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-benzaldehyde

HRID 1643695ノート

反応式

HRID 1643695 の反応式
N1C=CC=CC=1.[CH3:7][O:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]([CH2:30][OH:31])[CH:14]=[C:15]([O:26][CH2:27][O:28][CH3:29])[C:16]=1[CH2:17]/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[CH3:29][O:28][CH2:27][O:26][C:15]1[CH:14]=[C:13]([CH:12]=[C:11]([O:10][CH2:9][O:8][CH3:7])[C:16]=1[CH2:17]/[CH:18]=[CH:19]/[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH:30]=[O:31]

参加物

4

反応物 2

HCID 1049PyridineHCID 66755849[3,5-Bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-phenyl]-methanol

生成物 1

HCID 866247663,5-Bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-benzaldehyde収率 101.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of pyridine (62 g, 0.78 mol) in CH2Cl2 (500 mL) were added CrO3 (39 g, 0.39 mol) and Silica gel (40 g) in several portions at 0° C. After stirring for 10 min, [3,5-bis-methoxymethoxy-4-((E)-3-phenyl-allyl)-phenyl]-methanol (220e) (45 g, 0.13 mol) was added in one portion. The mixture was stirred at room temperature overnight. TLC (EtOAc/petroleum ether=1/2) indicated that the reaction was complete. The reaction mixture was filtered and the filter cake was washed with Et2O. The combined filtrates were concentrated. The residue was suspended in Et2O and filtered again. The filtrate was concentrated under vacuum to give the crude title compound (45 g, 100% yield) as a yellow oil, which was used directly in the next step without further purification. 1H NMR (400 MHz, CDCl3): δ 9.89 (s, 1H), 7.16-7.41 (m, 5H), 6.25˜6.44 (m, 2H), 5.36 (s, 4H), 3.66 (d, 2H), 3.47 (s, 6H).

後処理

  1. stirringThe mixture was stirred at room temperature overnight
  2. filtrationThe reaction mixture was filtered
  3. washthe filter cake was washed with Et2O
  4. concentrationThe combined filtrates were concentrated
  5. filtrationfiltered again
  6. concentrationThe filtrate was concentrated under vacuum

出典と根拠

ORDレコード
ord-8a307ba7c0d2494a91f812e2e1b5aac4
出典データセット
uspto-grants-2012_02
特許番号
US08119624B2

反応ノート

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