Tetrahydrofuran → 9-Benzyloxy-1-(2-methyl-pyrimidin-5-yl)-non-1-en-4-one

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Methylpyrimidine-5-carbaldehyde	HCID 3160970	—
Reactant	(7-Benzyloxy-2-oxo-heptyl)-phosphonic acid dimethyl ester	HCID 58765522	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	9-Benzyloxy-1-(2-methyl-pyrimidin-5-yl)-non-1-en-4-one	HCID 69666598	100%

Reaction Conditions

Temperature	60 °C

Reaction Steps

A mixture of 11-2 (4.4 g, 13.8 mmol), 2-methyl-pyrimidine-5-carbaldehyde (1.5 g, 12.5 mmol; for preparation, see J. Heterocyclic Chem., 28, 1281 (1991)) potassium carbonate (3.1 g, 25 mmol) and THF (200 mL) was heated at 60° C. for 3 hours. Following cooling, the mixture was diluted with ethyl acetate, washed with sat. NaHCO3 and brine, and dried over magnesium sulfate. Evaporation of the solvents gave 4.0 g (100%) of 11-3 as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07153862B2
Source dataset	uspto-grants-2006_12
ORD ID	ord-abab3968160a49ada81a85576cbb6761
Source note	uspto-grants-2006_12