Toluene → 2-[4-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]benzyloxy]nicotinaldehyde

HRID 1294175Notes

Reaction equation

HRID 1294175 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:30]=[CH:29][C:18]([CH2:19][O:20][C:21]2[N:28]=[CH:27][CH:26]=[CH:25][C:22]=2[C:23]#N)=[CH:17][CH:16]=1.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].C(OCC)(=[O:52])C>CCCCCC>[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:30]=[CH:29][C:18]([CH2:19][O:20][C:21]2[N:28]=[CH:27][CH:26]=[CH:25][C:22]=2[CH:23]=[O:52])=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 688859152-[4-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]benzyloxy]nicotinonitrile

Product 1

HCID 865915642-[4-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]benzyloxy]nicotinaldehydeYield 56%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a mixture of 2-[4-[(5-methyl-2-phenyl-4-thiazolyl)methoxy]benzyloxy]nicotinonitrile (4.18 g) and anhydrous toluene (150 mL) was dropwise added a solution (0.95 M, 23.4 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. 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 (2.35 g, 56%) of 2-[4-[(5-methyl-2-phenyl-4-thiazolyl)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: 101-102° C.

Workup

  1. stirringthe mixture was further stirred at room temperature for 15 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-8dbc389c4a7742ff9b5555d8eb5c799e
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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