Methyl iodide → Methyl 1-methoxycyclopropanecarboxylate

HRID 1695547Notes

Reaction equation

HRID 1695547 reaction equation
[OH:1][C:2]1([C:5]([O:7][CH3:8])=[O:6])[CH2:4][CH2:3]1.[H-].[Na+].I[CH3:12]>C1COCC1>[CH3:12][O:1][C:2]1([C:5]([O:7][CH3:8])=[O:6])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2733178Methyl 1-hydroxy-1-cyclopropane carboxylate

Product 1

HCID 20393514Methyl 1-methoxycyclopropanecarboxylateYield 54.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  1. temperaturecooled
  2. customThe mixture was quenched with saturated solution of NH4Cl (20 ml)
  3. extractionextracted with EtOAc
  4. customdried
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-b3bcf9abd66d4b6eae9b544b7fef80d4
Source dataset
uspto-grants-2012_04
Patent number
US08163724B2

Reaction notes

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