Nitrogen → 1-(5-(Hydroxymethyl)isoxazol-3-yl)ethanone

HRID 42817Notes

Reaction equation

N#N.C([SiH2][O:8][C:9](C)(C)[C:10]1[O:14][N:13]=[C:12]([C:15](=[O:17])[CH3:16])[CH:11]=1)(C)(C)C.COC(OC)OC.C([O-])(O)=O.[Na+]>C(O)CO>[OH:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([C:15](=[O:17])[CH3:16])[CH:11]=1

Participants

Conditions

Temperature: 95 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-isoxazol-3-yl]-ethanone (1.99 g, 7.79 mmol) in ethylene glycol (8.69 mL) was treated with trimethylorthoformate (1.71 mL, 15.58 mmol) followed by LiBF4 (146 mg, 1.56 mmol). The reaction mixture was heated at 95° C. overnight. Sat. aq. NaHCO3 (50 mL) was added and the mixture was extracted with EA (2×50 mL). The combined org. extracts were washed with brine (2×50 mL), dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (40:60 EA-Hept) gave the title compound as a yellow oil. TLC:rf (40:60 EA-Hept)=0.25. LC-MS-conditions 02: tR=0.54 min.

Workup

extractionthe mixture was extracted with EA (2×50 mL)
washextracts were washed with brine (2×50 mL)
dry with materialdried over MgSO4
filtrationfiltered
customthe solvent was removed under reduced pressure
customPurification of the residue by FC (40:60 EA-Hept)

Sources & evidence

ORD record: ord-e197fff6a28c41f1acf4b201bf710f83
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536209B2

Reaction notes

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