2-Methyl-3-buten-2-ol → HCID 22625558, compound

HRID 277654

Reaction equation

[CH3:1][C:2]([OH:6])([CH:4]=[CH2:5])[CH3:3].[CH3:7][Si:8]([SiH:11]([Si:16]([CH3:19])([CH3:18])[CH3:17])[Si:12]([CH3:15])([CH3:14])[CH3:13])([CH3:10])[CH3:9]>N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1>[CH3:1][C:2]([OH:6])([CH2:4][CH2:5][Si:11]([Si:12]([CH3:15])([CH3:14])[CH3:13])([Si:16]([CH3:19])([CH3:18])[CH3:17])[Si:8]([CH3:7])([CH3:9])[CH3:10])[CH3:3]

Participants

Conditions

Temperature: 110 °C

Procedure

A dried reaction flask equipped for magnetic stirring and fitted with a reflux condenser was flushed with nitrogen and charged with toluene (500 mL). Oxygen was purged from the system by passing a stream of nitrogen through the solvent, 2-methyl-3-buten-2-ol (43.1 g, 500 mmol), tris(trimethylsilyl)silane (25.0 g, 100 mmol), and 1,1′-azobis(cyclohexanecarbonitrile) (1.22 g, 5 mmol) were added to the flask, and the reaction mixture was heated for 20 hours at 110° C. with stirring. The resulting solution was concentrated under reduced pressure, and distillation under vacuum (bp 90-104° C. at 0.10 mm) afforded the title compound (25.1 g, 74%) as a colorless solid. The distilled product was characterized by the following NMR data: 1H NMR (CDCl3) δ 0.14 (s, 27 H), 0.70-0.80 (m, 2 H), 1.17 (s, 6 H), 1.30 (br s, 1 H), 1.45-1.55 (m, 2 H); 13C NMR (CDCl3) δ 1.06 (9 C), 1.24 (1 C), 28.35 (2 C), 42.99 (1 C), 71.64 (1 C); 29Si NMR (CDCl3) δ −80.90 (1 Si), −12.83 (3 Si).

Workup

customA dried reaction flask
customequipped
customfitted with a reflux condenser
customwas flushed with nitrogen
additioncharged with toluene (500 mL)
customOxygen was purged from the system
additionwere added to the flask
stirringwith stirring
concentrationThe resulting solution was concentrated under reduced pressure, and distillation under vacuum (bp 90-104° C. at 0.10 mm)

Sources & evidence

ORD record: ord-8b9aca523c30479c88171315d03aa37d
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06358675B1

Linked notes

Loading…