Dimethylformamide dimethyl acetal → Benzyl 2-[(dimethylamino)methylidene]-3-oxobutanoate

HRID 2202723Notes

Reaction equation

HRID 2202723 reaction equation
[O:1]=[C:2]([CH3:14])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>>[CH3:17][N:18]([CH:20]=[C:3]([C:2](=[O:1])[CH3:14])[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])[CH3:19]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 142266Benzyl acetoacetate

Product 1

HCID 68914059Benzyl 2-[(dimethylamino)methylidene]-3-oxobutanoate

Procedure

To a stirred benzyl 3-oxobutanoate (1.1 g, 5.7 mmol), dimethylformamide dimethylacetal (1 mL, 7.4 mmol) was added dropwise at room temperature. The mixture was stirred for 16 h at room temperature. The reaction mixture was concentrated under reduced pressure and the residue was azeotroped with toluene (3×10 mL) to provide compound D27-1 as a brown oil (1.4 g, quant.).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was azeotroped with toluene (3×10 mL)
  3. customto provide compound D27-1 as a brown oil (1.4 g, quant.)

Sources & evidence

ORD record
ord-c5a4c156a3e54100b2736a1efd26d52b
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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