Toluene → HCID 86591565, compound

HRID 1294186Notes

Reaction equation

HRID 1294186 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[C:4]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[N:21]=[C:22]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[O:23][C:24]=3[CH3:25])=[CH:14][CH:13]=2)[N:3]=1.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].C(OCC)(=[O:53])C>CCCCCC>[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:53])=[C:4]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:19][C:20]3[N:21]=[C:22]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[O:23][C:24]=3[CH3:25])=[CH:16][CH:17]=2)[N:3]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 68886253HCID 68886253, compound

Product 1

HCID 86591565HCID 86591565, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a mixture of 6-methyl-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinonitrile (1.70 g) and anhydrous toluene (80 mL) was dropwise added a solution (0.95 M, 9.5 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 (30 mL) was dropwise added to the mixture and the mixture was further stirred at room temperature for 30 min. Ethyl acetate was added to the mixture and, after stirring the mixture at room temperature for 30 min., 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 (0.98 g, 58%) of 6-methyl-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinaldehyde from a fraction eluted with ethyl acetate-hexane (1:6, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 114-115° C.

Workup

  1. stirringthe mixture was further stirred at room temperature for 30 min
  2. stirringafter stirring the mixture 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-227aefc2a07d4a2fa1263a00a1941bb1
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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