Dichloromethane → HCID 14769336, compound

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Dibenzyl ether	HCID 7657	—
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	HCID 178418373	HCID 178418373	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Product	HCID 14769336	HCID 14769336	—

Reaction Conditions

Temperature	-78 °C

Reaction Steps

To a mixture of the benzyl ether above (44 g, 0.268 mol) and CuI (51 g, 0.268 mol) in anhydrous THF (1 L) was slowly added MeMgI (270 mL of a 3 M THF solution, 0.810 mol) at -78° C. The mixture was stirred at -78° C. for 4 hours and was warmed to room temperature. After aqueous work-up (CH2Cl2) and chromatography, 47.0 g of the title compound was obtained: [α]25D +8.2° (c 1.2, CHCl3). IR: 3428. 1H NMR (CDCl3): δ0.94 (3H, t, J=7.5), 1.47 (2H, m), 2.38 (1H, br), 3.32 (1H, dd, J=8.0, 9.3), 3.50 (1H, dd, J=2.9, 9.3), 3.73 (1H, m), 4.54 (2H, s), 7.26-7.36 (5H, m). 13C NMR (CDCl3): δ9.8, 26.1, 71.7, 73.3, 74.3, 127.7, 127.7, 128.4, 138.0. HRMS (EI) calcd for C11H16O2 180.1150, found 180.1145.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05948770
Source dataset	uspto-grants-1999_09
ORD ID	ord-6ff5a446ab0f41fdbb1d34dbb84abc4d
Source note	uspto-grants-1999_09