Diethyl Ether → HCID 59339307, compound

HRID 12497

Reaction equation

HRID 12497 reaction equation
O.[NH2:2][NH2:3].C(OCC)C.[CH3:9][C:10](=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:11]=O>O>[CH3:9][CH:10]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:3][N:2]=[CH:11]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 75572-Methylcinnamic aldehydeHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 59339307HCID 59339307, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.22 ml (1 equiv.) hydrazine hydrate was added to 100 mL diethylether. The emulsion was cooled with an ice bath. 15.0 mL 2-Methyl-3-phenyl-propenal was added dropwise, and the mixture was stirred overnight at room temperature. H2O was added, the organic layer was separated and the aqueous layer was extracted with diethylether. The combined organic layers were dried over Na2SO4, filtrated and concentrated in vacuo. Vacuum distillation yielded 5.9 g of desired product (mixture of diastereomeric pairs) as a clear fluid (76-82° C., 0.2-0.3 mbar). 1H NMR (400 MHz, CDCl3) of first diastereomeric pair; δ 0.71 (d, J=7 Hz), 3H), 3.20-3.31 (m, 1H), 4.77 (d, J=10 Hz, 1H), 6.73 (br s, 1H), 7.23-7.42 (m, 5H), 8.55-8.60 (m, 2H). 1H NMR (400 MHz, CDCl3) of second diastereomeric pair: δ 1.24 (d, J=7 Hz), 3H), 2.90-3.11 (m, 1H), 4.22 (d, J=11 Hz, 1H), 6.71 (br s, 1H), 7.23-7.42 (m, 5H), 8.55-8.60 (m, 2H).

Workup

  1. temperatureThe emulsion was cooled with an ice bath
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with diethylether
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. distillationVacuum distillation

Sources & evidence

ORD record
ord-a7d533dfc1c64b57a8781969f0672fcd
Source dataset
uspto-grants-2010_06
Patent number
US07728018B2

Linked notes

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