Diethyl Ether → HCID 59339307, 화합물

HRID 12497

반응식

HRID 12497 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 59339307HCID 59339307, 화합물

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a7d533dfc1c64b57a8781969f0672fcd
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728018B2

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