Ethyl Acetoacetate → HCID 178472877, compound

HRID 75488Notes

Reaction equation

HRID 75488 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[N:10]([O-])=[O:11].[Na+]>C(O)(=O)C.O>[OH:11][N:10]=[C:2]([C:3](=[O:4])[CH3:5])[C:1]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 8868Ethyl Acetoacetate2×HCID 23668193Sodium Nitrite

Product 1

HCID 178472877HCID 178472877, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of ethyl acetoacetate (compound 7, 30 g, 0.23 mol) in acetic acid (35 mL) was added slowly sodium nitrite (18.0 g, 0.25 mol) in cold water (40 mL) at −10° C. The reaction mixture was stirred for 1 hr, then added cold water (120 mL) and stirred for 3 hrs. The mixture was extracted with diethyl ether (300 mL). The organic layer was washed with saturated NaHCO3 (400 mL×2), then dried over anhydrous MgSO4, filtered and concentrated in vacuo. The obtained product (21.46 g, white solid) was used for the next step without purification.

Workup

  1. stirringstirred for 3 hrs
  2. extractionThe mixture was extracted with diethyl ether (300 mL)
  3. washThe organic layer was washed with saturated NaHCO3 (400 mL×2)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe obtained product (21.46 g, white solid) was used for the next step without purification

Sources & evidence

ORD record
ord-38b8e18b3cb54831ab47c0f5dcaddc64
Source dataset
uspto-grants-2014_09
Patent number
US08835436B2

Reaction notes

Loading…