Pyrazole → 2-[(1S)-6-(1H-Pyrazol-1-yl)-3,4-dihydro-1H-2-benzopyran-1-yl]ethanol

https://huagongshe.com/reaction/2056781

Participants

Role	Name	HCID	Charge
Reactant	Pyrazole	HCID 1048	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol	HCID 53687843	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-[(1S)-6-(1H-Pyrazol-1-yl)-3,4-dihydro-1H-2-benzopyran-1-yl]ethanol	HCID 69307371	—

Reaction Conditions

Temperature	150 °C

Reaction Steps

2-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol (0.54 g, 2.1 mmol), pyrazole (0.29 g, 4.3 mmol), copper(I) iodide (0.062 g, 0.33 mmol) and potassium carbonate (0.30 g, 2.2 mmol) were stirred in dry DMF (3 mL) under nitrogen and heated at 150° C. for 18 h. The reaction mixture was cooled and extracted from water into dichloromethane. The combined organic extracts were dried (MgSO4), filtered and evaporated in vacuo. The crude product was used in the next step without further purification.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07335660B2
Source dataset	uspto-grants-2008_02
ORD ID	ord-8d3eba1569f34598ba8586f5a24c1918
Source note	uspto-grants-2008_02