Ethyl Acrylate → HCID 11300104, compound

HRID 520737Notes

Reaction equation

HRID 520737 reaction equation
[C:1]1([C:7](=NN)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C(C2C=CC=CC=2)=[N+]=[N-])C=CC=CC=1.[C:31]([O:35][CH2:36][CH3:37])(=[O:34])[CH:32]=[CH2:33]>[Hg]=O>[CH2:36]([O:35][C:31]([CH:32]1[CH2:33][C:7]1([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:34])[CH3:37]

Participants

5

Reactant 3

HCID 8821Ethyl AcrylateHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 79304Diphenylmethylidenehydrazine

Product 1

HCID 11300104HCID 11300104, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 30856Mercuric oxideCatalyst

Procedure

Diphenylketone hydrazone (3.92 g, 20 mmol) was mixed with yellow mercury oxide (4.33 g, 20 mmol) in 40 mL petroleum. The mixture was stirred at the temperature less than 20° C. for 16 hours. The deep red solution of diphenyl diazomethane in petroleum was added into ethyl acrylate (6.0 g, 60 mmol) at 50° C. in ten minutes. When the red colour fade off the solvent and excess of ethyl acrylate were removed under reduced pressure and the crude product obtained was further purified over silica chromatography to furnish 2,2-diphenylcyclopropanyl carboxylate ethyl ester 5.11 g (96% yield) as a pale yellow oil. 1H NMR (400 MHz, CDCl3): 7.36-7.17 (10H, m), 4.00-3.83 (2H, m), 2.54 (1H, dd, J=8.3, 6.0 Hz), 2.17 (1H, dd, J=1H, dd, 6.0, 4.8 Hz), 1.59 (1H, dd, J=8.3, 4.8 Hz), 1.01 (3H, t, J=7.1 Hz).

Workup

  1. customWhen the red colour fade off the solvent and excess of ethyl acrylate were removed under reduced pressure
  2. customthe crude product obtained
  3. customwas further purified over silica chromatography

Sources & evidence

ORD record
ord-fc20cde3c79a425da148d39b58d89f1c
Source dataset
uspto-grants-2016_05
Patent number
US09328074B2

Reaction notes

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