Lithium Hydroxide → HCID 59511115, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of cyclooctyne 8a (283 mg, 1.11 mmol) in dioxane (12 mL) and H2O (3 mL) was added finely crushed LiOH (530 mg, 22.1 mmol). The suspension was heated to 50° C. and stirred for 3 h. The dioxane was removed on a rotary evaporator. The residue was diluted with EtOAc (50 mL), washed with 1 N HCl (3×50 mL), H2O (3×50 mL), and brine (2×50 mL), and dried over MgSO4 to yield a white solid (254 mg, 95%, Rf=0.25 in 27:3:1 hexane/EtOAc/AcOH), mp 112.0-113.9° C. (dec). IR: 3071, 2922, 2846, 1680 cm−1. 1H NMR (CD3CN, 400 MHz): δ 1.35-1.48 (m, 2H), 1.56-1.66 (m, 1H), 1.66-1.95 (m, 4H), 2.01-2.17 (m, 3H), 2.70 (d, 1H, J=5.2 Hz), 2.71 (d, 1H, J=1.2 Hz), 2.76 (m, 1H), 7.33 (d, 2H, J=8.4 Hz), 7.91 (d, 2H, J=8.4 Hz), 9.40 (br s, 1H). 13C NMR (CD3CN, 100 MHz): δ 21.2, 29.2, 30.8, 35.6, 37.3, 40.8, 42.5, 95.7, 97.1, 128.9, 130.1, 130.5, 147.4, 167.8. EI-HRMS: Calcd. for C16H18O2M+: 242.1307. found: 242.1307. Anal. Calcd. for C16H18O2: C, 79.31; H, 7.49. Found: C, 79.07; H, 7.26.

Provenance & Evidence