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

HRID 1177220노트

반응식

HRID 1177220 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-53705dd6a40945acb755e0b03b82f27c
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842713B2

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