Sodium Hydroxide → 3-(1-Methoxy-2-methylpropan-2-YL)isoxazol-5-amine

HRID 469760Notes

Reaction equation

S(O)(O)(=O)=O.[OH:6][NH2:7].[CH3:8][O:9][CH2:10][C:11]([CH3:18])([CH3:17])[C:12](=O)[CH2:13][C:14]#[N:15].[OH-].[Na+]>O>[CH3:8][O:9][CH2:10][C:11]([C:12]1[CH:13]=[C:14]([NH2:15])[O:6][N:7]=1)([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 100 °C

Procedure

Hydroxyamine sulfate (1.56 g, 9.504 mmol) is added to a stirred solution of 5-methoxy-4,4-dimethyl-3-oxo-pentanenitrile (2.95 g, 19.008 mmol) and sodium hydroxide (1.635 g, 40.865 mmol) in water (40 mL). The reaction mixture is heated in 100° C. oil bath for 6 hours. After this time, the reaction mixture is diluted with water and extracted with ethyl acetate 3 times. The organics are combined and washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using methanol/methylene chloride provides the title compound, m/z 171 [M+H+].

Workup

extractionextracted with ethyl acetate 3 times
washwashed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by flash chromatography on silica gel

Sources & evidence

ORD record: ord-35125bcd78b44407bd4275d7b7d6e45f
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629157B2

Reaction notes

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