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

HRID 1177220ノート

反応式

HRID 1177220 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-53705dd6a40945acb755e0b03b82f27c
出典データセット
uspto-grants-2010_11
特許番号
US07842713B2

反応ノート

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