Sodium Hydroxide → 2-(5-Methyl-2-phenyl-4-oxazolyl)ethanol

HRID 505489Notes

Reaction equation

HRID 505489 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[N:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:8][C:9]=1[CH3:10].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>CCOCC.O>[CH3:10][C:9]1[O:8][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:6][C:5]=1[CH2:4][CH2:3][OH:2]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 2775318Methyl (5-methyl-2-phenyl-1,3-oxazol-4-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanolYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

(5-Methyl-2-phenyl-1,3-oxazol-4-yl)-acetic acid methyl ester (2.3 g, 10 mmol) was dissolved in 16 mL of Et2O, and then added dropwise at 0° C. to a suspension of LiAlH4 (0.38 g, 10 mmol) in Et2O (4 mL). The solution was stirred at room temperature overnight, to which 0.4 mL H2O, 0.4 mL of 15% NaOH solution, and 1.2 mL of H2O, and a spoon of anhydrous MgSO4 were carefully added in turn. The mixture was filtered, and the filtrate was concentrated to give 1.6 g of 2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)-ethanol as a jasmine solid with a yield of 80%.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5d63a5941c324bfd948a2440ee46d325
Source dataset
uspto-grants-2010_08
Patent number
US07781468B2

Reaction notes

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