Methyl iodide → Ethyl 2-methoxymethyl-2,3-dihydrobenzofuran-5-carboxylate

HRID 256400Notes

Reaction equation

HRID 256400 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][C:6]2[CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=[CH:11][C:5]=2[O:4]1.[H-].[Na+].[CH3:19]I>O1CCCC1>[CH3:19][O:1][CH2:2][CH:3]1[CH2:7][C:6]2[CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=[CH:11][C:5]=2[O:4]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13728720Ethyl 2-hydroxymethyl-2,3-dihydrobenzofuran-5-carboxylate

Product 1

HCID 20163636Ethyl 2-methoxymethyl-2,3-dihydrobenzofuran-5-carboxylateYield 85.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2.5 g (11.26 mmole) ethyl 2-hydroxymethyl-2,3-dihydrobenzofuran-5-carboxylate in 50 ml tetrahydrofuran was cooled under nitrogen to 0° C. and 595 mg (12.38 mmole) of a 50% by weight dispersion of sodium hydride in oil was added in portions. The mixture was stirred to 0° C. for 15 minutes, then a solution of 1.756 g (12.38 mmole) methyl iodide in 30 ml tetrahydrofuran was added dropwise. The resulting mixture was allowed to warm to room temperature and stirred overnight. The mixture was concentrated in vacuo, the residue partitioned between ethyl ether and water. The ether extracts were combined, washed with brine, dried (MgSO4) and the solvent evaporated in vacuo to yield 2.28 g of product as an oil. 1H-NMR(CDCl3) showed singlet at 3.4 ppm, consistent with the presence of a CH2OCH3 group.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue partitioned between ethyl ether and water
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-c8ccdcf65784417c8f09b4707cc987eb
Source dataset
uspto-grants-1987_10
Patent number
US04703052

Reaction notes

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