Dimethylformamide → HCID 178420383, compound

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Azidotrimethylsilane	HCID 78378	—
Reactant	4'-Benzyloxyphenyl acetylene	HCID 1490323	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Methanol	HCID 887	—
Product	HCID 178420383	HCID 178420383	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

Trimethylsilyl azide (415 mg, 3.6 mmol) was added to a DMF (4.3 mL) and MeOH (0.48 mL) solution containing CuI (22.9 mg, 0.12 mmol) and 1-(benzyloxy)-4-ethynylbenzene (500 mg, 2.4 mmol) under Ar in a pressure tube (caution: build-up of pressure possible; use a safety shield). The reaction mixture was stirred at 100° C. for 12 h. The mixture was cooled to room temperature and filtered through a short silica gel pad and concentrated. The residue was purified by recrystallization from DCM.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08343990B2
Source dataset	uspto-grants-2013_01
ORD ID	ord-57629a30725e489cb4bcd5f5837562dd
Source note	uspto-grants-2013_01