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

HRID 1274471Notes

Reaction equation

HRID 1274471 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.

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-6924d8e313e4485b80ef9e9833a31e6f
Source dataset
uspto-grants-2000_12
Patent number
US06156748

Reaction notes

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