Water → 2-(3,5-Di-t-butyl-4-hydroxyphenyl)-4-(2-hydroxyethyl)-5-methyloxazole

HRID 618521Notes

Reaction equation

HRID 618521 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[O:17][C:18]([CH3:27])=[C:19]([CH2:21][C:22](OCC)=[O:23])[N:20]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[O:17][C:18]([CH3:27])=[C:19]([CH2:21][CH2:22][OH:23])[N:20]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 135725057[2-(3,5-Di-tert-butyl-4-hydroxyphenyl)-5-methyloxazol-4-yl]-acetic acid ethyl ester

Product 1

HCID 1357250762-(3,5-Di-t-butyl-4-hydroxyphenyl)-4-(2-hydroxyethyl)-5-methyloxazoleYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Starting ester, the compound of Step B 4.43 g (11.88 mmole), was dissolved in 83 ml tetrahydrofuran with stirring, under nitrogen. Solid lithium aluminum hydride (LAH), 450 mg (11.88 mmole), was cautiously added. There was much bubbling. The mixture was stirred 30 minutes and another 225 mg (5.94 mmole) lithium aluminum hydride was added and the reaction stirred under nitrogen overnight. Water (0.675 ml) was cautiously added followed by 0.675 ml 15% sodium hydroxide, followed by 2.0 ml water. The inorganics were filtered off and the filtrate was stripped, dissolved in ethyl acetate, washed once with 1 N hydrochloric acid, twice with brine, and stripped to give 3.61 g (92%) of product which was used without further purification. FDMS--M+=331 NMR (CDCl3), δ 1.48 (s, 18H), 2.32 (s, 3H), 2.73 (t, 2H, J=4 Hz), 3.91 (t, 2H, J=4 Hz), 5.51 (s, 1H), 7.81 (s, 2H)

Workup

  1. stirringThe mixture was stirred 30 minutes
  2. stirringthe reaction stirred under nitrogen overnight
  3. filtrationThe inorganics were filtered off
  4. dissolutiondissolved in ethyl acetate
  5. washwashed once with 1 N hydrochloric acid, twice with brine

Sources & evidence

ORD record
ord-be267cdf5f1040209b17a9f873ecc681
Source dataset
uspto-grants-1999_09
Patent number
US05952360

Reaction notes

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