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

HRID 1792391Notes

Reaction equation

HRID 1792391 reaction equation
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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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%

Sources & evidence

ORD record
ord-618d76bb37f04bedb7d1a9a4b5ec1dd6
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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