3-Bromo-5-(1-hydroxypropyl)isoxazole → 1-(3-Bromo-1,2-oxazol-5-yl)ethan-1-one

Reaction equation

COC1C=C(C(O)C)ON=1.[Br:11][C:12]1[CH:16]=[C:15]([CH:17]([OH:20])[CH2:18]C)[O:14][N:13]=1.BrC1C=C(C(O)CCC)ON=1>>[Br:11][C:12]1[CH:16]=[C:15]([C:17](=[O:20])[CH3:18])[O:14][N:13]=1

Participants

Reactant 3

HCID 138020893-Bromo-5-(1-hydroxypropyl)isoxazole

HCID 138020903-Bromo-5-(1-hydroxybutyl)-isoxazole

HCID 212922791-(3-Methoxyisoxazol-5-YL)ethan-1-OL

Product 1

HCID 136269711-(3-Bromo-1,2-oxazol-5-yl)ethan-1-one

Procedure

In a similar manner 3-methoxy-5-(1-hydroxyethyl)-isoxazole, 3-bromo-5-(1-hydroxypropyl)-isoxazole and 3-bromo-5-(1-hydroxybutyl)-isoxazole were oxidized to afford

Workup

customto afford

Sources & evidence

ORD record: ord-037ecdf04a4d436b8e1f063d314741d7
Source dataset: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04772719

Reaction notes

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