N,N,N',N'-Tetramethylethylenediamine → 4-(hydroxymethyl)-3,4-dihydro-2H-chromene-8-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	N,N,N',N'-Tetramethylethylenediamine	HCID 8037	—
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	(8-bromo-3,4-dihydro-2H-chromen-4-yl)methanol	HCID 67516017	—
Catalyst	Zinc cyanide (Zn(CN)2)	HCID 11186	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-(hydroxymethyl)-3,4-dihydro-2H-chromene-8-carbonitrile	HCID 67516964	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

A solution of (8-bromo-3,4-dihydro-2H-chromen-4-yl)methanol (1 g, 4.12 mmol) in 3 mL of DMF was added Zn(CN)2 (481 mg, 4.12 mmol), Pd2(dba)3 (67 mg, 0.04 mmol), TMEDA (191 mg, 1.6 mmol), Xantphose (48 mg, 0.08 mmol), and the mixture was stirred under microwave irradiation for 5 min at 100° C. The mixture was added with 10 mL of EtOAc, washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep-TLC to give 4-(hydroxymethyl)-3,4-dihydro-2H-chromene-8-carbonitrile.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09056859B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-74a2ab077706474a9f188b275b8fb0f3
Source note	uspto-grants-2015_06