Diketene → HCID 59327641, compound

HRID 538749Notes

Reaction equation

HRID 538749 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:14])([CH3:13])[C:9]([NH:11][NH2:12])=[O:10])=[CH:4][CH:3]=1.[CH2:15]=[C:16]1[O:19][C:18](=[O:20])[CH2:17]1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:14])([CH3:13])[C:9]([NH:11][NH:12][C:18](=[O:20])[CH2:17][C:16](=[O:19])[CH3:15])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12661DiketeneHCID 59327639HCID 59327639, compound

Product 1

HCID 59327641HCID 59327641, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-chlorophenyl)-2-methylpropanehydrazide (9.0 g, 42.5 mmol) was dissolved in dry tetrahydrofuran (100 ml), and 4-methyleneoxetan-2-one (3.9 ml, 51 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 18 hours, then solvent removed under rescued pressure, and ethyl acetate was added. The solution was passed through a 120 g silica gel column eluting with ethyl acetate, to provide clean N′-(2-(4-chlorophenyl)-2-methylpropanoyl)-3-oxobutanehydrazide (12.2 g, 97%) as a viscous golden oil. TLC Rf=0.47 using 100% ethyl acetate as eluent on a glass backed silica gel plate.

Workup

  1. customsolvent removed under rescued pressure, and ethyl acetate
  2. additionwas added
  3. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-23dec032942a43a990400979258e36cf
Source dataset
uspto-grants-2014_10
Patent number
US08865739B2

Reaction notes

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