Hydrochloric Acid → HCID 28344998, compound

HRID 1912037Notes

Reaction equation

HRID 1912037 reaction equation
C([O:3][CH:4](OCC)[CH2:5][NH:6][C:7](=[O:11])[CH2:8][CH2:9][CH3:10])C.Cl.CCOCC.O>C1COCC1>[O:3]=[CH:4][CH2:5][NH:6][C:7](=[O:11])[CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 79548415HCID 79548415, compound

Product 1

HCID 28344998HCID 28344998, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N-(2,2-diethoxyethyl)butyramide (2.0 g, 0.0098 mol.)) in 10 mL of THF at 0° C. was added HCl(2N) in ether (4.9 mL, 1.0 eq) and water (0.34 mL, 2 eq). The solution was then stirred for 2 to 3 h at 0° C. the solvent was evaporated at room temperature and solid NaHCO3 was added, filtration and concentration to give after silica gel chromatography N-(2-oxoethyl)butyramide as a colorless oil (0.55 g g, 55% yield). 1HNMR (400 MHz, CDCl3): δ 0.89 (t, J=7.2 Hz, 3H); 1.58-1.63 (m, 2H); 2.12 (t, J=7.2 Hz, 2H); 4.17 (d, J=5.2 Hz, 2H); 6.31 (sbroad, 1H); 9.63 (s, 1H).

Workup

  1. customwas evaporated at room temperature
  2. additionsolid NaHCO3 was added
  3. filtrationfiltration and concentration

Sources & evidence

ORD record
ord-ee8b6be1a10e4017a893d7efba65dae3
Source dataset
uspto-grants-2013_12
Patent number
US08604244B2

Reaction notes

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