Methanol → HCID 68887116, compound

HRID 1294188Notes

Reaction equation

HRID 1294188 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[CH:28]=[CH:27][C:24]([CH:25]=O)=[C:23]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]3[N:40]=[C:41]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[O:42][C:43]=3[CH3:44])=[CH:33][CH:32]=2)[N:22]=1.CO>C(COC)OC.O>[CH3:20][C:21]1[N:22]=[C:23]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]3[N:40]=[C:41]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[O:42][C:43]=3[CH3:44])=[CH:33][CH:32]=2)[C:24]([CH2:25][C:16]#[N:17])=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 23665647Potassium tert-butoxideHCID 53627694Toluenesulfonylmethyl isocyanideHCID 86591565HCID 86591565, compound

Product 1

HCID 68887116HCID 68887116, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a mixture of potassium t-butoxide (0.47 g) and dimethoxyethane (8 mL) was added a solution (8 mL) of toluenesulfonylmethylisocyanide (0.43 g) in dimethoxyethane at −78° C. Furthermore, a solution (8 mL) of 6-methyl-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinaldehyde (0.84 g) in dimethoxyethane was added to the reaction mixture. The reaction mixture was stirred at −78° C. for 1 hr. Methanol (10 mL) was added to the reaction mixture at room temperature and the mixture was heated under reflux for 30 min. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel, column chromatography to give crystals (0.67 g, 79%) of 2-[6-methyl-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetonitrile from a fraction eluted with ethyl acetate-hexane (1:6, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 122-123° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-062cb853853f4c38b81614a54746aa44
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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