Benzaldehyde → 1,4-Pentadien-3-one, 1-(4-methoxyphenyl)-5-phenyl-, (E,E)-

HRID 77677

반응식

HRID 77677 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=1.[OH-].[Na+].O.[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11](=[O:13])[CH:12]=[CH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 240BenzaldehydeHCID 962WaterHCID 14798Sodium HydroxideHCID 954144-(4-Methoxyphenyl)but-3-en-2-one

생성물 1

HCID 7605101,4-Pentadien-3-one, 1-(4-methoxyphenyl)-5-phenyl-, (E,E)-수율 96.9%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

1-(4-Methoxyphenyl)-1-buten-3-one (35e, 0.29 g, 1.6 mmol) was dissolved in methanol (5 ml) and stirred for 5 min at room temperature. A solution of sodium hydroxide (0.14 g, 3.5 mmol) and water (5 ml) was added and the mixture stirred for 30 min at room temperature. Benzaldehyde (1b, 0.17 ml, 1.7 mmol) was added dropwise and the mixture stirred for 18 hr at room temperature. The resulting precipitate was filtered and recrystallized from ethanol to give 0.41 g (94%) of a yellow solid: mp 85-89° C. [expected mp 118-119° C.]; 1H NMR: δ 3.82 (s, 3H), 6.91 (d, 2H, J=8.5 Hz), 6.94 (d, 1H, J=15.9 Hz), 7.06 (d, 1H, J=16.1 Hz), 7.38 (m, 4H), 7.57 (m, 3H), 7.71 (dd, 2H, J=15.9, 2.0 Hz); 13C NMR: δ 55.4, 114.4, 123.3, 125.5, 127.4, 128.2, 128.8, 130.0, 130.2, 134.8, 142.6, 143.0, 161.5, 188.6.

후처리

  1. stirringthe mixture stirred for 30 min at room temperature
  2. stirringthe mixture stirred for 18 hr at room temperature
  3. filtrationThe resulting precipitate was filtered
  4. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-5f6605a5b4044f2f810367de70af7ec3
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841326B2

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