Methyl iodide → Methyl 3-[2-(methyloxy)ethyl]-1-naphthalenecarboxylate

HRID 337600Notes

Reaction equation

HRID 337600 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2.I[CH3:19].[H-].[Na+]>C1COCC1>[CH3:19][O:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66896170Methyl 3-(2-hydroxyethyl)-1-naphthalenecarboxylate

Product 1

HCID 66896973Methyl 3-[2-(methyloxy)ethyl]-1-naphthalenecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-(2-hydroxyethyl)-1-naphthalenecarboxylate (1 eq.) from the previous step and iodomethane (19 eq.) were taken up in THF (0.3 M). To this solution was then added sodium hydride (60% w/w dispersion in oil, 1 eq.) and the resulting suspension was stirred at RT in darkness for 18 h. The volatiles were then removed in vacuo and the resulting residue partitioned between ether and 1 N aq. HCl. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were then washed further with 1 N aq. NaOH, water and brine. This was then dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford a yellow oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 19:1 (v/v) Hex:EtOAc→1:1 (v/v) EtOAc:Hex) afforded the title compound as a pale yellow oil.

Workup

  1. customThe volatiles were then removed in vacuo
  2. customthe resulting residue partitioned between ether and 1 N aq. HCl
  3. customThe aqueous layer was separated
  4. extractionback-extracted with ether
  5. washThe combined organic extracts were then washed further with 1 N aq. NaOH, water and brine
  6. dry with materialThis was then dried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo
  9. customto afford a yellow oil
  10. customPurification of the crude product
  11. customthus obtained by way of flash chromatography (SiO2, 19:1 (v/v) Hex:EtOAc→1:1 (v/v) EtOAc:Hex)

Sources & evidence

ORD record
ord-1f429d53e3a24456a1a50f9d16ba44bf
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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