P-Xylene → 4'-Acetoxy-3,5-bis(methoxymethoxy)stilbene

HRID 2236329

반응식

HRID 2236329 반응식
CC1C=CC(C)=CC=1.[CH3:9][O:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([O:22][CH2:23][O:24][CH3:25])[CH:21]=1)[C:16](Cl)=O.[C:26]([O:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=C)=[CH:32][CH:31]=1)(=[O:28])[CH3:27].CN1CCOCC1>[Pd].[Cl-].C(C1C=CC=C(C(C)C)C=1[NH+]1CCN(C2C(C(C)C)=CC=CC=2C(C)C)C1)(C)C.CCOC(C)=O>[C:26]([O:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=[CH:16][C:15]2[CH:14]=[C:13]([O:12][CH2:11][O:10][CH3:9])[CH:21]=[C:20]([O:22][CH2:23][O:24][CH3:25])[CH:19]=2)=[CH:32][CH:31]=1)(=[O:28])[CH3:27]

참가 물질

8

반응물 4

HCID 7809P-XyleneHCID 79724-MethylmorpholineHCID 758214-Ethenylphenyl acetateHCID 593017303,5-Bis(methoxymethoxy)benzoyl chloride

생성물 1

HCID 671702434'-Acetoxy-3,5-bis(methoxymethoxy)stilbene수율 59%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 184547821,3-BIS(2,6-DIISOPROPYLPHENYL)imidazoLIDINIUM-CHLORIDE촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

A 50 mL round bottom flask was charged with p-xylene (20 mL), Pd II catalyst (22.5 mg, 0.1 mmol), 1,3-bis-(2,6-diisopropylphenyl) imidazolinium chloride (42.7 mg, 0.1 mmol), 3,5-bis(methoxymethoxy)benzoyl chloride (2.42 g, 10 mmol), 4-acetoxystyrene (1.94 g, 12 mmol), and N-methyl morpholine (1.38 g, 12 mmol). The mixture was stirred at 120° C. for 3.5 h under nitrogen atmosphere. Then it was cooled to room temperature and EtOAc was added and filtered. The filtrate was washed with brine and dried over Na2SO4. Then it was filtered and purified via flash chromatography and gave the product (2.1 g, 59%) as white solid. Data are: 1H NMR (CDCl3, 300 MHz) δ 7.48 (d, 2H), 7.08-6.93 (m, 4H), 6.86 (d, 2H), 6.66 (t, 1H), 5.19 (s, 4H), 3.50 (s, 6H), 2.30 (s, 3H); 13C NMR (CDCl3, 75 MHz) δ 169.5, 158.7, 150.3, 139.5, 135.0, 128.7, 128.5, 127.6, 121.9, 108.0, 104.5, 94.6, 56.2, 21.2; HRMS (EI+) found 358.1409 M+, calcd 358.1416 for C20H22O6.

후처리

  1. temperatureThen it was cooled to room temperature
  2. filtrationfiltered
  3. washThe filtrate was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationThen it was filtered
  6. custompurified via flash chromatography

출처 및 근거

ORD 기록
ord-7257de764c6d48af958cc133ae028272
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07714161B2

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