Ammonia → 3-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole

HRID 1504798Notes

Reaction equation

[CH3:1][C:2]1[C:6]([B:7]2[O:11][C:10]([CH3:13])([CH3:12])[C:9]([CH3:15])([CH3:14])[O:8]2)=[C:5]([Si](C)(C)C)[O:4][N:3]=1.N>C(O)C>[CH3:1][C:2]1[C:6]([B:7]2[O:11][C:10]([CH3:13])([CH3:12])[C:9]([CH3:15])([CH3:14])[O:8]2)=[CH:5][O:4][N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a sealed vessel were charged 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trimethylsilyl)isoxazole (169 g, 0.569 mol), 25% aqueous ammonia (1500 mL), and ethanol (1500 mL). The reaction mixture was heated to 60° C. After 6 hours, the reaction mixture was concentrated under reduced pressure. The residue was purified via chromatography on silica gel (0-5% methanol/dichloromethane, linear gradient) to give 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole. MS ESI calc'd. for C10H16BNO3 [M]+ 209. found 209. 1H NMR (400 MHz, CDCl3) δ 8.54 (s, 1H), 2.40 (s, 3H), 1.31 (s, 12H).

Workup

concentrationthe reaction mixture was concentrated under reduced pressure
customThe residue was purified via chromatography on silica gel (0-5% methanol/dichloromethane, linear gradient)

Sources & evidence

ORD record: ord-1c60f4b5a03344d282548127fc2a52b1
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216173B2

Reaction notes

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