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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1695547Generated: November 1, 2026

Methyl iodide → Methyl 1-methoxycyclopropanecarboxylate

https://huagongshe.com/reaction/1695547

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantSodium hydrideHCID 24758—
ReactantMethyl 1-hydroxy-1-cyclopropane carboxylateHCID 2733178—
SolventTetrahydrofuranHCID 8028—
ProductMethyl 1-methoxycyclopropanecarboxylateHCID 2039351454.8%

Reaction Steps

According to WO 2005/014577 methyl 1-hydroxycyclopropanecarboxylate (1.01 g, 8.70 mmol) was dissolved under argon in THF (10 ml) and cooled using an ice-bath. Sodium hydride (60%, 0.52 g, 13.00 mmol) was added portionwise followed by iodomethane (1 ml, 16.06 mmol) and the mixture was stirred for 18 hours at room temperature. The mixture was quenched with saturated solution of NH4Cl (20 ml) and extracted with EtOAc. The organic extracts were combined, dried, filtered and evaporated in vacuo to give 620 mg of the crude product which was used as such.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08163724B2
Source datasetuspto-grants-2012_04
ORD IDord-b3bcf9abd66d4b6eae9b544b7fef80d4
Source noteuspto-grants-2012_04