Triethylamine → (Z)-tert-Butyl(1-(3-chlorophenyl)pent-1-enyloxy)dimethylsilane

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	tert-Butyldimethylsilyl trifluoromethanesulphonate	HCID 123564	—
Reactant	1-Chloro-3-[(1Z)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-propen-1-yl]-benzene	HCID 11300561	—
Solvent	Dichloromethane	HCID 6344	—
Product	(Z)-tert-Butyl(1-(3-chlorophenyl)pent-1-enyloxy)dimethylsilane	HCID 46838071	96%

Reaction Steps

Compound 9t was synthesized by a procedure similar to that described for 9a using 3-chloropentaphenone (8k, 2.7 g, 0.014 mol), TBDMSOTf (3.5 mL, 15 mmol), and Et3N (3.1 mL) in CH2Cl2 (25 mL). After purification, 4.18 g (96%) of the title product was isolated as colorless oil: 1H NMR (CDCl3) δ 7.47-7.44 (m, 1H), 7.38-7.32 (m, 1H), 7.30-7.28 (m, 1H), 7.25-7.22 (m, 1H), 5.18 (t, 1H, J=7.2 Hz), 2.20 (q, 2H, J=7.5 Hz), 1.54-1.38 (m, 2H), 1.02 (s, 9H), 1.00-0.90 (m, 3H), −0.05 (s, 6H); 13C NMR (CDCl3) δ 148.0, 141.8, 133.9, 129.2, 127.6, 125.9, 123.9, 113.0, 28.3, 25.8, 22.8, 14.0, 0.0, −4.01. C17H27ClOSi.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08906908B2
Source dataset	uspto-grants-2014_12
ORD ID	ord-2fd5c9ebd35443b7b949bdc4d5abff7e
Source note	uspto-grants-2014_12