Formaldehyde → tert-butyl N-but-3-enyl-N-(2-oxobut-3-enyl)carbamate

HRID 523626Notes

Reaction equation

HRID 523626 reaction equation
[CH2:1]([N:5]([CH2:13][C:14](=[O:35])[CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:2][CH:3]=[CH2:4].[CH2:36]=O>C1COCC1>[CH2:1]([N:5]([CH2:13][C:14](=[O:35])[CH:15]=[CH2:36])[C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH2:2][CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 118222052Tert-butyl but-3-en-1-yl(2-oxo-3-(triphenylphosphoranylidene)propyl)carbamate

Product 1

HCID 118222042tert-butyl N-but-3-enyl-N-(2-oxobut-3-enyl)carbamateYield 49.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
18 °C

Procedure

To a mixture of tert-butyl N-but-3-enyl-N-[2-oxo-3-(triphenyl-phosphanylidene) propyl]carbamate (5.80 g, 11.90 mmol, 1.00 Eq) in THF (30 mL), was added HCHO (96.58 g, 1.19 mol, 100.00 Eq) in one portion at 18° C. The mixture was stirred at 18° C. for 15 hr. TLC showed the reaction was completed. The mixture was extracted with PE (100 mL*3). The combined organic phase was washed with saturated brine (200 mL*2), dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography (PE/EA=50/1, 40/1) to afford tert-butyl N-but-3-enyl-N-(2-oxobut-3-enyl)carbamate (1.40 g, 5.85 mmol, 49.16% yield) as yellow solid.

Workup

  1. extractionThe mixture was extracted with PE (100 mL*3)
  2. washThe combined organic phase was washed with saturated brine (200 mL*2)
  3. dry with materialdried with anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customThe residue was purified by silica gel chromatography (PE/EA=50/1, 40/1)

Sources & evidence

ORD record
ord-87b3931401ce48a4bdaaab617862a1d4
Source dataset
uspto-grants-2016_05
Patent number
US09339510B2

Reaction notes

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