Tetrahydrofuran → Methyl 1-methoxycyclopropanecarboxylate

HRID 225451Notes

Reaction equation

HRID 225451 reaction equation
[CH3:1][O:2][C:3]([C:5]1([OH:8])[CH2:7][CH2:6]1)=[O:4].[H-].[Na+].O1CCC[CH2:12]1>>[CH3:1][O:2][C:3]([C:5]1([O:8][CH3:12])[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 2733178Methyl 1-hydroxy-1-cyclopropane carboxylate

Product 1

HCID 20393514Methyl 1-methoxycyclopropanecarboxylate

Conditions

Temperature
0 °C

Procedure

1-Hydroxy-cyclopropanecarboxylic acid methyl ester (1.1 6 gm, 10 mmol) was dissolved in 10 ml of tetrahydrofuran and cooled under a nitrogen atmosphere to 0° C. Sodium hydride (0.52 gm, 60% oil dispersion) was added portionwise followed by lodomethane (1 ml) and stirred for 18 hrs. The reaction mixture was quenched with ammonium chloride and extracted with ethylacetate to obtain 2 gm of title product. (MH+=130)

Workup

  1. customThe reaction mixture was quenched with ammonium chloride
  2. extractionextracted with ethylacetate

Sources & evidence

ORD record
ord-4c0eaa4519af4bed8bf24e4e60c5bad6
Source dataset
uspto-grants-2009_07
Patent number
US07557107B2

Reaction notes

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