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Tetrahydrofuran → {2-(3-Hydroxy-5-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester

HRID 1161379
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HRID 1161379 반응식
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.[CH3:24][O:25][C:26](=[O:64])[N:27]=[C:28]([S:62][CH3:63])[C:29]([C:43]1[CH:48]=[C:47]([O:49][Si](C(C)C)(C(C)C)C(C)C)[CH:46]=[C:45]([O:60][CH3:61])[CH:44]=1)=[N:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[N:41]=[C:40]([CH3:42])[O:39][N:38]=2)=[CH:33][CH:32]=1.[Cl-].[NH4+]>C(OCC)(=O)C>[CH3:24][O:25][C:26](=[O:64])[N:27]=[C:28]([S:62][CH3:63])[C:29]([C:43]1[CH:44]=[C:45]([O:60][CH3:61])[CH:46]=[C:47]([OH:49])[CH:48]=1)=[N:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[N:41]=[C:40]([CH3:42])[O:39][N:38]=2)=[CH:33][CH:32]=1
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참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 72312779{2-(3-Methoxy-5-triisopropylsilanyloxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester

생성물 1

HCID 72312820{2-(3-Hydroxy-5-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester
수율 79.8%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

After adding 3.3 ml of TBAF (1.0 M, THF solution) to a 15 ml THF solution containing 1.8 g of {2-(3-methoxy-5-triisopropylsilanyloxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester, the mixture was stirred at 0° C. for 1 hour and 30 minutes. Saturated aqueous ammonium chloride was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (1.06 g) as a yellow solid.

후처리

  1. washThe organic layer was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

출처 및 근거

ORD 기록
ord-b74352da10084956a5f85af44cbcd06b
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07816522B2

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