Nitrogen → 2-(4-Methylisoxazol-3-yl)ethanol

Participants

Reaction Steps

A solution of (Z)-3-(tert-butyldimethylsilyloxy)-N-hydroxypropanimidoyl chloride (90 mg, 0.378 mmol) in ClCH2CH2Cl (Volume: 2 mL) at room temperature was purged with N2 for 2 min. Prop-1-yne (0.022 mL, 0.378 mmol) [Condensed at −78° C.] was added as a liquid, followed by chloro(1,5-cyclooctadiene)(pentamethylcyclopentadienyl)ruthenium (II) (7.17 mg, 0.019 mmol) and triethylamine (0.066 mL, 0.473 mmol). The reaction mixture was stirred at room temperature for 16 h. It was dark brown in color. The mixture was filtered through 0.45 μm membrane. The filtrate was concentrated, diluted with MeOH, and purified with prep HPLC (Waters Xbridge C18 19×100 mm), 20 mL/min flow rate with gradient of 30% B-100% B over 10 minutes Hold at 100% B for 2 min. (A: 0.1% TFA in water/MeOH (90:10), B: 0.1% TFA in water/MeOH (10:90) monitoring at 220 nm. After concentration, 2-(4-methylisoxazol-3-yl)ethanol (35 mg, 0.270 mmol, 71.3% yield) was obtained as light brown liquid. 1H NMR (400 MHz, chloroform-d) δ 8.13 (s, 1H), 4.03 (t, J=5.9 Hz, 2H), 2.89 (t, J=5.9 Hz, 2H), 2.02 (d, J=0.9 Hz, 3H).

Provenance & Evidence