Tetrahydrofuran → (R)-4-methyl-4-(6-(4-pentylcyclohexyloxy)naphthalen-2-yl)oxazolidin-2-one

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	4-Pentylcyclohexanol	HCID 41076	—
Reactant	Diisopropyl diazene-1,2-dicarboxylate	HCID 75555	—
Reactant	(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one	HCID 51066623	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	(R)-4-methyl-4-(6-(4-pentylcyclohexyloxy)naphthalen-2-yl)oxazolidin-2-one	HCID 67413569	68.4%

Reaction Steps

(R)-4-(6-Hydroxnaphthalen-2-yl)-4-methyl-oxazolidin-2-one (Example 4, 0.3303 g, 0.001358 mol) was added to a capped 40 mL vial equipped with a magnetic stir bar. 4-Pentyl-cyclohexanol (0.277 g, 0.00163 mol) was added, followed by tetrahydrofuran (6.00 mL, 0.0740 mol). Triphenylphosphine polymer-bound (1.17 g, 0.00217 mol) was then added and the mixture was stirred for 5 minutes. Diisopropyl azodicarboxylate (0.428 mL, 0.00217 mol) was then added and the mixture was stirred for 48 hours at room temperature. The mixture was diluted in ethyl acetate, filtered through CELITE™, concentrated under vacuum and purified by flash chromatography (0-5% MeOH in dichloromethane) to give 0.3672 g of the title compound (68% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08546359B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-e9105e36287c4fff8baf3f4d99ba2793
Source note	uspto-grants-2013_10