3-Methyl-2-butenoyl chloride → HCID 69217131, compound

HRID 899284Notes

Reaction equation

HRID 899284 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH3:2].[CH3:19][C:20]([CH3:25])=[CH:21][C:22](Cl)=[O:23]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][C:22](=[O:23])[CH:21]=[C:20]([CH3:25])[CH3:19])[CH:12]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH3:2]

Participants

4

Reactant 2

HCID 1023943-Methyl-2-butenoyl chlorideHCID 69214221HCID 69214221, compound

Product 1

HCID 69217131HCID 69217131, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-(3-amino-phenyl)-heptanoic acid ethyl ester (3.866 g, 15.5 mmole) in 40 mL of chloroform was treated with 1.73 mL of 3,3-dimethylacryloyl chloride. The mixture was heated at reflux for four hours, quenched by the addition of 100 mL water and extracted with three 50 mL portions of chloroform. The combined organic extracts were washed with 100 mL of saturated aqueous sodium bicarbonate solution, 100 mL of water and 100 mL of saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The product was purified by flash chromatography (SiO2, 15% ethyl acetate in hexanes) to yield 3.822 g of 2-[3-(3-methyl-but-2-enoylamino)-phenyl]-heptanoic acid ethyl ester as a pale yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for four hours
  3. customquenched by the addition of 100 mL water
  4. extractionextracted with three 50 mL portions of chloroform
  5. washThe combined organic extracts were washed with 100 mL of saturated aqueous sodium bicarbonate solution, 100 mL of water and 100 mL of saturated aqueous sodium chloride solution
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a yellow oil
  10. customThe product was purified by flash chromatography (SiO2, 15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8729a3d669f447ecb3eb96b9c92e62f3
Source dataset
uspto-grants-2008_04
Patent number
US07354931B2

Reaction notes

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