Methyl iodide → Methyl 1-methoxycyclopentane-1-carboxylate

HRID 626533Notes

Reaction equation

HRID 626533 reaction equation
[H-].[Na+].[OH:3][C:4]1([C:9]([O:11][CH3:12])=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5]1.I[CH3:14]>C1COCC1>[CH3:14][O:3][C:4]1([C:9]([O:11][CH3:12])=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 244662Methyl 1-hydroxycyclopentane-1-carboxylate

Product 1

HCID 67529636Methyl 1-methoxycyclopentane-1-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A 0° C. suspension of NaH (60% in mineral oil, 0.644 g, 16.09 mmol) (pre-washed with hexanes, 2×) in THF (10 mL) was treated slowly with a solution of methyl 1-hydroxycyclopentanecarboxylate (1.45 g, 10.06 mmol) in THF (10 mL), stirred at 0° C. for 15 min, treated with iodomethane (1.258 mL, 20.12 mmol), warmed to RT and stirred overnight. The mixture was poured into satd. NH4Cl, extracted with EtOAc (3×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford methyl 1-methoxycyclopentanecarboxylate (1.0 g, 63%). 1H NMR (400 MHz, CDCl3): δ 3.76 (s, 3H), 3.24 (s, 3H), 1.98-1.96 (m, 4H), 1.76-1.74 (m, 4H).

Workup

  1. temperaturewarmed to RT
  2. stirringstirred overnight
  3. additionThe mixture was poured into satd
  4. extractionNH4Cl, extracted with EtOAc (3×)
  5. washthe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-39f3afd495c34722b19e2745843c569a
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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