Hydroxyamine hydrochloride → 5-Tert-butylisoxazole

HRID 254837Notes

Reaction equation

HRID 254837 reaction equation
ClC1C=CC(C2N(C3C=CC(Cl)=CC=3Cl)N=C([C:21](=[O:29])/[CH:22]=[C:23](\[OH:28])/[C:24]([CH3:27])([CH3:26])[CH3:25])C=2C)=CC=1.Cl.[NH2:32]O>CCO>[C:24]([C:23]1[O:28][N:32]=[CH:21][CH:22]=1)([CH3:27])([CH3:26])[CH3:25].[C:24]([C:23]1[CH:22]=[CH:21][O:29][N:32]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 178429089HCID 178429089, compound

Product 2

HCID 33043535-Tert-butylisoxazoleYield 34%HCID 137402333-(1,1-Dimethylethyl)isoxazoleYield 14%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of diketone (87) (200 mg, 0.43 mmol) and hydroxylamine hydrochloride (60 mg, 0.86 mmol) in EtOH (5 mL) was irradiated in a microwave reactor (Biotage) for 20 min. at 140° C. Purification by Prep-LC (Gilson) provided 67 mg (34%) of 5-t-butylisoxazole and 28 mg (14%) of 3-t-butylisoxazole as solid.

Workup

  1. customPurification by Prep-LC (Gilson)

Sources & evidence

ORD record
ord-7a44d0548f024378b6ec41fd317817b8
Source dataset
uspto-grants-2011_01
Patent number
US07875647B2

Reaction notes

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