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

HRID 1792391
ノート
印刷プレビュー

反応式

HRID 1792391 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887
Methanol
溶媒
HCID 962Water溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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%

出典と根拠

ORDレコード
ord-618d76bb37f04bedb7d1a9a4b5ec1dd6
出典データセット
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07074819B2

反応ノート

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