Toluene → HCID 86760507, compound

HRID 1294172Notes

Reaction equation

HRID 1294172 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:29])=[C:9]([CH2:11][O:12][C:13]2[CH:28]=[CH:27][C:16]([CH2:17][O:18][C:19]3[N:26]=[CH:25][CH:24]=[CH:23][C:20]=3[C:21]#N)=[CH:15][CH:14]=2)[N:10]=1.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].C(OCC)(=[O:51])C>CCCCCC>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:29])=[C:9]([CH2:11][O:12][C:13]2[CH:28]=[CH:27][C:16]([CH2:17][O:18][C:19]3[N:26]=[CH:25][CH:24]=[CH:23][C:20]=3[CH:21]=[O:51])=[CH:15][CH:14]=2)[N:10]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 68885963HCID 68885963, compound

Product 1

HCID 86760507HCID 86760507, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a mixture of 2-[4-[[2-(2-furyl)-5-methyl-4-oxazolyl]methoxy]benzyloxy]nicotinonitrile (4.50 g) and anhydrous toluene (150 mL) was dropwise added a solution (0.95 M, 25.5 mL) of diisobutylaluminum hydride in hexane at −78° C. The reaction mixture was allowed to warm to room temperature with stirring for 1 hr. A saturated aqueous ammonium chloride solution (50 mL) was dropwise added to the mixture and the mixture was further stirred at room temperature for 15 min. To this mixture was added ethyl acetate and the mixture was stirred at room temperature for 30 min., and then insoluble materials were filtered off. The filtrate was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (2.60 g, 57%) of 2-[4-[[2-(2-furyl)-5-methyl-4-oxazolyl]methoxy]benzyloxy]nicotinaldehyde from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 109-110° C.

Workup

  1. stirringthe mixture was further stirred at room temperature for 15 min
  2. stirringthe mixture was stirred at room temperature for 30 min.
  3. filtrationinsoluble materials were filtered off
  4. washThe filtrate was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d5e94391fb3847799b3c902b27e5668b
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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