Toluene → 2-[4-[[2-(2-Furyl)-5-methyl-4-oxazolyl]methoxy]-3-methoxybenzyloxy]-3-pyridinecarbaldehyde

HRID 1294225Notes

Reaction equation

HRID 1294225 reaction equation
[C:1]([C:3]1[C:4]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[N:20]=[C:21]([C:25]4[O:26][CH:27]=[CH:28][CH:29]=4)[O:22][C:23]=3[CH3:24])=[C:13]([O:30][CH3:31])[CH:12]=2)=[N:5][CH:6]=[CH:7][CH:8]=1)#N.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].C(OCC)(=[O:53])C>CCCCCC>[O:26]1[CH:27]=[CH:28][CH:29]=[C:25]1[C:21]1[O:22][C:23]([CH3:24])=[C:19]([CH2:18][O:17][C:14]2[CH:15]=[CH:16][C:11]([CH2:10][O:9][C:4]3[C:3]([CH:1]=[O:53])=[CH:8][CH:7]=[CH:6][N:5]=3)=[CH:12][C:13]=2[O:30][CH3:31])[N:20]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 688834623-Cyano-2-[4-[[2-(2-furyl)-5-methyl-4-oxazolyl]methoxy]-3-methoxybenzyloxy]pyridine

Product 1

HCID 865915762-[4-[[2-(2-Furyl)-5-methyl-4-oxazolyl]methoxy]-3-methoxybenzyloxy]-3-pyridinecarbaldehydeYield 16%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a mixture of 3-cyano-2-[4-[[2-(2-furyl)-5-methyl-4-oxazolyl]methoxy]-3-methoxybenzyloxy]pyridine (6.30 g) and anhydrous toluene (250 mL) was dropwise added a solution (0.95 M, 47 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 reaction mixture at 0° C. and ethyl acetate was further added. Insoluble materials were filtered off and the filtrate 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 crystals (1.0 g, yield 16%) of 2-[4-[[2-(2-furyl)-5-methyl-4-oxazolyl]methoxy]-3-methoxybenzyloxy]-3-pyridinecarbaldehyde from a fraction eluted with ethyl acetate-hexane (2:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 120-121° C.

Workup

  1. filtrationInsoluble materials were filtered off
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ad5e831e68854f3580c2c603b763590c
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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