Lithium Hydroxide → HCID 59511115, compound

HRID 1774260Notes

Reaction equation

C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C:13]#[C:12]2)=[CH:6][CH:5]=1.[Li+].[OH-]>O1CCOCC1.O>[CH:11]1([CH2:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:19])=[O:2])=[CH:9][CH:8]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C:13]#[C:12]1

Participants

Conditions

Temperature: 50 °C

Procedure

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.

Workup

customThe dioxane was removed on a rotary evaporator
additionThe residue was diluted with EtOAc (50 mL)
washwashed with 1 N HCl (3×50 mL), H2O (3×50 mL), and brine (2×50 mL)
dry with materialdried over MgSO4
customto yield a white solid (254 mg, 95%, Rf=0.25 in 27:3:1 hexane/EtOAc/AcOH), mp 112.0-113.9° C. (dec)

Sources & evidence

ORD record: ord-aaf97ea7ecb1425b9b6ea1230f656577
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260371B2

Reaction notes

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