Methyl iodide → Methyl 1-methoxycyclopropanecarboxylate

HRID 626530Notes

Reaction equation

HRID 626530 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]>CN(C=O)C>[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 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A 0° C. solution of methyl 1-hydroxycyclopropane-1-carboxylate (1 g, 8.61 mmol) in DMF (10 mL) was treated with NaH (60% in mineral oil, 0.689 g, 17.22 mmol), stirred at 0° C. for 0.5 h, treated with iodomethane (0.646 mL, 10.33 mmol), allowed to slowly warm to RT and stirred for 2 h. The mixture was quenched with satd. NH4Cl, diluted with water and extracted with Et2O (3×). The combined organics were washed with water, then brine, dried and concentrated to afford methyl 1-methoxycyclopropane-1-carboxylate (1.10 g, 98%). 1H NMR (400 MHz, DMSO-d6): δ 3.62 (s, 3H), 3.27 (s, 3H), 1.12-1.11 (m, 4H).

Workup

  1. temperatureto slowly warm to RT
  2. stirringstirred for 2 h
  3. customThe mixture was quenched with satd
  4. additionNH4Cl, diluted with water
  5. extractionextracted with Et2O (3×)
  6. washThe combined organics were washed with water
  7. dry with materialbrine, dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-19bf978b6317485cb332d52f583df81c
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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