Methyl iodide → Ethyl 6-(1-benzenesulphonylethyl)-3-ethyl-2-methoxybenzoate

HRID 2177689Notes

Reaction equation

HRID 2177689 reaction equation
[H-].[Na+].[C:3]1([S:9]([CH2:12][C:13]2[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:17]([O:24][CH3:25])[C:16]([CH2:26][CH3:27])=[CH:15][CH:14]=2)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.I[CH3:29].[Cl-].[NH4+]>CN(C=O)C.O>[C:3]1([S:9]([CH:12]([C:13]2[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:17]([O:24][CH3:25])[C:16]([CH2:26][CH3:27])=[CH:15][CH:14]=2)[CH3:29])(=[O:11])=[O:10])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67107794Ethyl 6-(benzenesulphonylmethyl)-3-ethyl-2-methoxybenzoate2×

Product 1

HCID 67107928Ethyl 6-(1-benzenesulphonylethyl)-3-ethyl-2-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% oil dispersion, 0.009 g) was added to a stirred and cooled solution of ethyl 6-(benzenesulphonylmethyl)-3-ethyl-2-methoxybenzoate (Intermediate 20, 0.075 g) in DMF (1 ml) at 0° C. under an atmosphere of nitrogen. After stirring for 15 minutes iodomethane (0.014 ml) was added and the resultant mixture was stirred at room temperature for 1 hour. Ammonium chloride (saturated aqueous solution) was added followed by water and the mixture was extracted with ethyl acetate, washed with water, brine, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-20% to give ethyl 6-(1-benzenesulphonylethyl)-3-ethyl-2-methoxybenzoate (0.063 g) as a colourless oil.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-20%

Sources & evidence

ORD record
ord-7070dc76988c4146956989005c0b5c21
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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