Tetrahydrofuran → Methyl 6-(2-methoxyethoxymethoxy)naphthalene-2-carboxylate

HRID 969475

Reaction equation

HRID 969475 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([C:14]([O:16][CH3:17])=[O:15])[CH:8]=[CH:7]2.O1CCCC1.[CH3:23][O:24][CH2:25][CH2:26][O:27][CH2:28]Cl>CN(C)C=O>[CH3:23][O:24][CH2:25][CH2:26][O:27][CH2:28][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([C:14]([O:16][CH3:17])=[O:15])[CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 390995Methyl 6-hydroxy-2-naphthoate

Product 1

HCID 12085484Methyl 6-(2-methoxyethoxymethoxy)naphthalene-2-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.3 g (83 mmol) of 60% sodium hydride in oil are added portionwise to a solution of 14 g (69 mmol) of methyl 6-hydroxynaphthalene-2-carboxylate in 180 ml of an equivolume mixture of tetrahydrofuran and dimethylformamide. After the evolution of gas has ceased, 8.7 ml (76 mmol) of methoxyethoxymethyl chloride are added dropwise. The reaction medium is stirred at room temperature for 3 hours, immersed into ice-cold water and extracted with ethyl ether. The organic phase is dried over sodium sulfate, filtered and concentrated under vacuum. The residue obtained is purified by chromatography on a column of silica eluted with an 80/20 heptane/ethyl acetate mixture. 17 g of methyl 6-(2-methoxyethoxymethoxy)naphthalene-2-carboxylate are obtained in the form of a colorless oil, in a yield of 85%.

Workup

  1. extractionextracted with ethyl ether
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with an 80/20 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-46d1260935e44f699670d3851c25d14e
Source dataset
uspto-grants-2007_12
Patent number
US07307078B2

Linked notes

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