Methanol → HCID 68884253, compound

HRID 1294230Notes

Reaction equation

HRID 1294230 reaction equation
CC(C)([O-])C.[K+].C1(C)C(S([CH2:16][N+:17]#[C-])(=O)=O)=CC=CC=1.[CH3:20][C:21]1[O:25][C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:23][C:22]=1[CH2:32][O:33][C:34]1[CH:35]=[C:36]([CH:47]=[CH:48][CH:49]=1)[CH2:37][S:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][CH:46]=1)[CH:42]=O.CO>C(COC)OC>[CH3:20][C:21]1[O:25][C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:23][C:22]=1[CH2:32][O:33][C:34]1[CH:35]=[C:36]([CH:47]=[CH:48][CH:49]=1)[CH2:37][S:38][C:39]1[CH:40]=[C:41]([CH2:42][C:16]#[N:17])[CH:44]=[CH:45][CH:46]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 23665647Potassium tert-butoxideHCID 53627694Toluenesulfonylmethyl isocyanideHCID 86591572HCID 86591572, compound

Product 1

HCID 68884253HCID 68884253, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

To a mixture of potassium t-butoxide (0.38 g) and dimethoxyethane (10 mL) was added a solution of toluenesulfonylmethylisocyanide (0.33 g) in dimethoxyethane (5 mL) at −78° C. and the mixture was stirred for 10 min. A solution (10 mL) of 3-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzylthio]benzaldehyde (0.70 g) in dimethoxyethane was added to the reaction mixture and the mixture was stirred for 30 min at −78° C. Methanol (25 mL) was added to the reaction mixture at room temperature and the mixture was heated under reflux for 1 hr. The reaction mixture was concentrated, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 2-[3-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzylthio]phenyl]acetonitrile as an oil (0.295 g, yield 41%) from a fraction eluted with acetone-hexane (1:5, v/v).

Workup

  1. stirringthe mixture was stirred for 30 min at −78° C
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hr
  4. concentrationThe reaction mixture was concentrated
  5. additionwater was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b2dca73a5683400b9fb0946b584b68ed
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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