Triphenylphosphine → 3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-2,2-dimethyl-propionic acid methyl ester

https://huagongshe.com/reaction/20761

Participants

Role	Name	HCID	Charge
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	Diisopropyl diazene-1,2-dicarboxylate	HCID 75555	—
Reactant	Methyl 3-hydroxypivalate	HCID 84152	—
Reactant	4-hydroxy-2,3-dihydro-1H-isoindole-1,3-dione	HCID 346002	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-2,2-dimethyl-propionic acid methyl ester	HCID 59348026	33.6%

Reaction Conditions

Temperature	0 °C

Reaction Steps

To methyl hydroxypivalate (1.31 g, 9.89 mmol) were added tetrahydrofuran (40 ml), hydroxyphthalimide (3.23 g, 19.78 mmol) and triphenylphosphine (6.48 g, 24.73 mmol). After this solution was cooled to 0° C., diisopropyl azodicarboxylate (4.87 ml, 24.73 mmol) was added dropwise to the solution. While being allowed to warm gradually, the reaction mixture was stirred for 12 hours, and concentrated under reduced pressure. The residue was roughly purified by silica gel column chromatography to give the title compound (922 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07745663B2
Source dataset	uspto-grants-2010_06
ORD ID	ord-97c9716f95c14692a5ef32b3dbd750ba
Source note	uspto-grants-2010_06