Citric Acid → HCID 69298909, compound

HRID 131294Notes

Reaction equation

HRID 131294 reaction equation
[CH2:1]([N:3]([CH2:6]C)[CH2:4][CH3:5])C.[CH3:8]S(Cl)(=O)=O.[C:13](O)(=O)[CH2:14][C:15]([CH2:20][C:21](O)=O)([C:17]([OH:19])=[O:18])O.O1CC[CH2:28][CH2:27]1>C(OCC)(=O)C>[CH3:6][N:3]([CH3:1])[CH2:4][CH:5]=[CH:27][C:28]1[CH:21]=[CH:20][C:15]([C:17]([O:19][CH3:8])=[O:18])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 69298909HCID 69298909, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound obtained in the above step (1) (200 mg) in tetrahydrofuran (4 mL) is added triethylamine (218 μL) and methanesulfonyl chloride (105 μL) under ice-cooling and the mixture is stirred for 30 minutes. The reaction mixture is diluted with ethyl acetate and thereto is added 10% citric acid solution. The mixture is extracted with ethyl acetate and the extract is washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. To the residue is dissolved in dimethylformamide (2 mL) and thereto is added 2M dimethylamine/tetrahydrofuran (2 mL). The mixture is stirred at room temperature for 2 days. The reaction mixture is diluted with ethyl acetate, washed with a saturated sodium hydrogencarbonate solution, and concentrated in vacuo. The residue purified by column chromatography on silica gel (Solvent; chloroform:methanol=100:0→90:10) to give methyl 4-[3-(dimethylamino)-1-propenyl]-benzoate (198 mg, yield; 87%) as an oil. MS (APCI) m/z; 220 [M+H]+

Workup

  1. temperaturecooling
  2. extractionThe mixture is extracted with ethyl acetate
  3. washthe extract is washed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. dissolutionTo the residue is dissolved in dimethylformamide (2 mL)
  7. additionis added 2M dimethylamine/tetrahydrofuran (2 mL)
  8. stirringThe mixture is stirred at room temperature for 2 days
  9. additionThe reaction mixture is diluted with ethyl acetate
  10. washwashed with a saturated sodium hydrogencarbonate solution
  11. concentrationconcentrated in vacuo
  12. customThe residue purified by column chromatography on silica gel (Solvent; chloroform:methanol=100:0→90:10)

Sources & evidence

ORD record
ord-69fd675d63cf491dbaffe28042a6a172
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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