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Sodium Methoxide → 4-[9-(4-Cyanobutylthio)nonyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

HRID 1792391
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HRID 1792391 반응식
C(OCCCCC#N)(=S)C.C[O-].[Na+].CS(O[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]1[C:37]2[C:32](=[CH:33][C:34]([O:38][CH3:39])=[CH:35][CH:36]=2)[S:31][CH2:30][C:29]1([C:41]1[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=1)[CH3:40])(=O)=O.[C:49]([CH2:51][CH2:52][CH2:53][CH2:54][SH:55])#[N:50]>CO.O1CCCC1.O>[C:49]([CH2:51][CH2:52][CH2:53][CH2:54][S:55][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]1[C:37]2[C:36](=[CH:35][C:34]([O:38][CH3:39])=[CH:33][CH:32]=2)[S:31][CH2:30][C:29]1([C:41]1[CH:42]=[CH:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=1)[CH3:40])#[N:50]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 10942334Sodium MethoxideHCID 220331154-(9-Methanesulfonyloxynonyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochromanHCID 220331875-SulfanylpentanenitrileHCID 541226084-Cyanobutyl thioacetate

생성물 1

HCID 220330614-[9-(4-Cyanobutylthio)nonyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

시약·촉매·용매 3

HCID 887
Methanol
용매
HCID 962Water용매
HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-cyanobutyl thioacetate (613 mg, 3.90 mmol) in methanol (10 ml) and was added 1M sodium methoxide (3.06 ml) and stirred at room temperature for 1 h. Then (3RS,4RS)-4-(9-methansulfonyloxynonyl)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman (290 mg, 0.557 mmol) dissolved in dry tetrahydrofuran (5 ml) was added dropwise thereto at room temperature and stirred overnight. When the reaction was completed, water was added to the reaction solution which was then extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The residue was concentrated under reduced pressure and flash chromatographed on silica gel (n-hexane:ethyl acetate=8:2) to give 495 mg (165%, contains the 4-cyanobutan-1-thiol) of the title compound as a colorless oil.

후처리

  1. additionwas added dropwise
  2. stirringat room temperature and stirred overnight
  3. extractionwas then extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe residue was concentrated under reduced pressure and flash
  7. customchromatographed on silica gel (n-hexane:ethyl acetate=8:2)
  8. customto give 495 mg (165%

출처 및 근거

ORD 기록
ord-618d76bb37f04bedb7d1a9a4b5ec1dd6
출처 데이터셋
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07074819B2

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