Sodium Sulfate → [5-[3-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]methanol

HRID 1294151Notes

Reaction equation

HRID 1294151 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([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:13]=2)[CH:7]=[N:6][CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:25][C:24]1[O:23][C:22]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[N:21][C:20]=1[CH2:19][O:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[CH2:11][O:10][C:8]1[CH:9]=[C:4]([CH2:3][OH:2])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 68885855Methyl 5-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinate

Product 1

HCID 68884421[5-[3-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]methanolYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl-5-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinate (0.50 g) and tetrahydrofuran (10 mL) was added lithium aluminum hydride (0.045 g) under ice-cooling, and the mixture was stirred at room temperature for 3 hrs. Sodium sulfate 1.0 hydrate (0.39 g) was added to the mixture and the mixture was further stirred at room temperature for 30 min. The insoluble materials were removed by filtration, and the filtrate was concentrated to give crystals (0.47 g, 98%) of [5-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]methanol. Recrystallization from ethyl acetate-hexane gave colorless needle crystals. melting point: 145-146° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred at room temperature for 30 min
  3. customThe insoluble materials were removed by filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a002c584ca6f42438fe1375a1e9390a2
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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