Hydrochloric Acid → HCID 131730028, compound

HRID 2065956Notes

Reaction equation

HRID 2065956 reaction equation
[CH2:1](/[C:3](=[CH:7]\[C:8](=[O:10])[CH3:9])/[C:4]([NH2:6])=[O:5])[CH3:2].O.[BH4-].[Na+].Cl>CO>[CH2:1](/[C:3](=[CH:7]\[CH:8]([OH:10])[CH3:9])/[C:4]([NH2:6])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 131730027HCID 131730027, compound

Product 1

HCID 131730028HCID 131730028, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

24 (ethyl (2E)-4-oxopent-2-enamide) (5.18 g, 36.7 mmol) is dissolved in MeOH (6 ml) and H2O (54 ml) and cooled to 0° C. NaBH4 is added to the resulting solution (426 mg, 11.3 mmol) in portions over 15 min. After 30 min of additional stirring at 0° C., the reaction mixture is acidified with 2 M HCl (1.15 ml) and extracted with AcOiPr (2×1 l). The organic phases are washed with brine (2×25 ml). The combined organic phases are dried with Na2SO4 and evaporated under reduced pressure at 40° C. The residue is purified by flash chromatography (MeOH:CH2Cl2 5:95 to 7.5:92.5) and yields 25 (rac-Ethyl (2E)-4-hydroxypent-2-enamide) (4.60 g, 88%) as a viscous brown oil.

Workup

  1. extractionextracted with AcOiPr (2×1 l)
  2. washThe organic phases are washed with brine (2×25 ml)
  3. dry with materialThe combined organic phases are dried with Na2SO4
  4. customevaporated under reduced pressure at 40° C
  5. customThe residue is purified by flash chromatography (MeOH:CH2Cl2 5:95 to 7.5:92.5)

Sources & evidence

ORD record
ord-1c623ffc38a047d8af310a6c3e80e46e
Source dataset
uspto-grants-2012_10
Patent number
US08288566B2

Reaction notes

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