Nitrogen → (2-(2-Methyl-[1,3]dioxolan-2-yl)oxazol-4-yl)methanol

HRID 1044763Notes

Reaction equation

N#N.C([O:5][C:6]([C:8]1[N:9]=[C:10]([C:13]2([CH3:18])[O:17][CH2:16][CH2:15][O:14]2)[O:11][CH:12]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1.O>[CH3:18][C:13]1([C:10]2[O:11][CH:12]=[C:8]([CH2:6][OH:5])[N:9]=2)[O:17][CH2:16][CH2:15][O:14]1

Participants

Conditions

Temperature: 0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to an ice-cold solution of 2-(2-methyl-[1,3]dioxolan-2-yl)-oxazole-4-carboxylic acid ethyl ester (5.05 g, 22.2 mmol) in dry THF (80 mL) was added an ice-cold solution of LiAlH4 (1.0 M in THF, 24.7 mL, 24.7 mmol). The reaction mixture was stirred at 0° C. until completion of the reaction. Water (2.0 mL) was carefully added at 0° C. followed by aq. 1 M NaOH (2.0 mL) and water (2.0 mL). The resulting suspension was stirred at rt for 1 h, filtered (+EA) and the filtrate concentrated under reduced pressure to give the title compound as a yellow oil. TLC: rf (EA)=0.18. LC-MS-conditions 05c: tR=0.22 min; [M+H]+=186.30.

Workup

stirringThe resulting suspension was stirred at rt for 1 h
filtrationfiltered (+EA)
concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record: ord-44a6f4e341a94c2c802883bf2b2b098d
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563714B2

Reaction notes

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