1,2-Dimethoxyethane → HCID 10335035, compound

HRID 2245802Notes

Reaction equation

HRID 2245802 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:16])[C:5]1[CH:15]=[CH:14][C:8]2[S:9][C:10]([CH:12]=O)=[CH:11][C:7]=2[CH:6]=1.[C:17]([O:20][CH2:21][CH3:22])(=[O:19])[CH3:18].CO[CH2:25][CH2:26]OC>>[CH2:21]([O:20][C:17](=[O:19])/[CH:18]=[CH:25]/[CH:26]=[CH:12]/[C:10]1[S:9][C:8]2[CH:14]=[CH:15][C:5]([N:4]([CH3:16])[CH3:3])=[CH:6][C:7]=2[CH:11]=1)[CH3:22]

Participants

5

Reactant 4

HCID 80711,2-Dimethoxyethane3×HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 11600896HCID 11600896, compound

Product 1

HCID 10335035HCID 10335035, compoundYield 65%

Procedure

To a mixture of sodium hydride (60% in mineral oil, 128 mg, 3.2 mmol) in ethylene glycol dimethyl ether (4 mL) was added dropwise at 0° C. a solution of triethyl phosphonocrotonate (800 mg, 3.2 mmol) in ethylene glycol dimethyl ether (2 mL). The mixture was stirred at room temperature for 45 min. A solution of 5-dimethylamino-benzo[b]thiophene-2-carboxaldehyde (596 mg, 2.9 mmol) in ethylene glycol dimethyl ether (5 mL) was added in dropwise manner. The mixture was stirred at reflux for 90 min, cooled to room temperature and diluted by addition of ethyl acetate (50 mL). The mixture was washed with water (3×25 mL) and brine (25 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give an oil, that was purified by flash chromatography (10:90:1 ethyl acetate:40-60° C. petroleum ether:triethylamine) to give a solid that was recrystallised from ethanol to give the title compound (567 mg, 65%) as a solid, mp 140-142° C.

Workup

  1. stirringThe mixture was stirred
  2. temperatureat reflux for 90 min
  3. temperaturecooled to room temperature
  4. washThe mixture was washed with water (3×25 mL) and brine (25 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give an oil, that
  9. customwas purified by flash chromatography (10:90:1 ethyl acetate:40-60° C. petroleum ether:triethylamine)
  10. customto give a solid
  11. customthat was recrystallised from ethanol

Sources & evidence

ORD record
ord-d65e7d97c18d4840a0ad53b727e2ab8a
Source dataset
uspto-grants-2010_03
Patent number
US07683185B2

Reaction notes

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