Ethyl chloroformate → 3-(3,4-Dimethoxyphenyl)propanamide

HRID 2414815Notes

Reaction equation

HRID 2414815 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]([OH:15])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].ClC(OCC)=O.[OH-].[NH4+:23]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]([NH2:23])=[O:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 14923Ammonium HydroxideHCID 750193-(3,4-Dimethoxyphenyl)propionic acid

Product 1

HCID 8833563-(3,4-Dimethoxyphenyl)propanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-15 °C

Procedure

To a stirred solution of 3-(3,4-dimethoxy-phenyl)-propionic acid (10.0 g, 47.6 mmol) in dry THF (175 mL), under nitrogen, is added TEA (7.3 ml, 52.4 mmol). The resulting mixture is cooled to −10° C. before ethyl chloroformate (5.0 ml, 52 mmol) is added dropwise. After stirring at −10° C. (20 min), ammonium hydroxide (25% in water, 105 ml) in THF (105 mL) is added and the mixture is stirred at −15° C. for 30 min and then at rt for 1.5 h. The reaction mixture is concentrated in vacuo, extracted three times with CH2Cl2 and the combined organic extracts are washed with saturated aqueous NaHCO3 and brine. The organic phase is dried over anhydrous MgSO4, filtered and concentrated to give the title compound as a colorless solid.

Workup

  1. additionis added dropwise
  2. additionis added
  3. waitat rt for 1.5 h
  4. concentrationThe reaction mixture is concentrated in vacuo
  5. extractionextracted three times with CH2Cl2
  6. washthe combined organic extracts are washed with saturated aqueous NaHCO3 and brine
  7. dry with materialThe organic phase is dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-10d835c5c49e494d9c84b905c4312b24
Source dataset
uspto-grants-2004_11
Patent number
US06815451B2

Reaction notes

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