Ethyl 2-formylbutanoate → HCID 178437179, compound

HRID 2374737Notes

Reaction equation

HRID 2374737 reaction equation
[Na].Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([NH2:14])=[NH:13])=[CH:6][CH:5]=1.[CH:15]([CH:17]([CH2:23][CH3:24])[C:18](OCC)=O)=[O:16]>C(O)C>[CH2:23]([C:17]1[C:15](=[O:16])[N:13]=[C:12]([CH2:11][CH2:10][C:7]2[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=2)[NH:14][CH:18]=1)[CH3:24]

Participants

5

Reactant 3

HCID 289299Ethyl 2-formylbutanoateHCID 5360545SodiumHCID 69157575HCID 69157575, compound

Product 1

HCID 178437179HCID 178437179, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (0.23 g) in dry ethanol (10 ml) was treated with 3-(4-fluorophenyl)propionamidine hydrochloride (Int. A108) (1.02 g). Ethyl 2-formylbutyrate (0.72 g) was added and the mixture refluxed for 6 h then maintained at room temperature for a further 24 h. The reaction mixture was concentrated in vacuo, and the residue treated with water and acidified with conc. hydrochloric acid. The white precipitate was filtered off, washed with water and dried in vacuo at 40° C. overnight, to give the title compound, (982 mgs, 80%) 1H-NMR (CDCl3) δ 1.22 (3H, t), 2.52 (2H, q), 2.94 (2H, m), 3.09 (2H, m), 6.96 (2H, m), 7.24 (2H, m), 7.84 (1H, s) and 13.06 (1H, br. s). (APCI+) Found (M+1)=247, C14H15FN2O requires 246.

Workup

  1. temperaturethe mixture refluxed for 6 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionthe residue treated with water
  4. filtrationThe white precipitate was filtered off
  5. washwashed with water
  6. customdried in vacuo at 40° C. overnight

Sources & evidence

ORD record
ord-5bf7e8f3ea234f40be6d351c7324dc6f
Source dataset
uspto-grants-2008_12
Patent number
US07462620B2

Reaction notes

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