Ammonium Chloride → 7-Octen-2-one

HRID 1879245노트

반응식

HRID 1879245 반응식
[CH3:1][Mg]Br.CON(C)[C:7](=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[CH3:1][C:7](=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13]

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 46703846N-methoxy-N-methylhept-6-enamideHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 193157-Octen-2-one수율 96%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

Methyl magnesium bromide (3M in ether, 3 eq.) was added dropwise to a stirred mixture of N-methoxy-N-methylhept-6-enamide 58 in THF (0.1 M) cooled at 0° C. After sting for 1 h at 0° C., the mixture was poured into sat. aq. NH4Cl and diluted with EtOAc. The aqueous layer was further extracted with EtOAc, the combined organic layers were washed with brine and dried (Na2SO4). Evaporation of the solvent at 30 mbar afforded the title compound (96%) as a colorless oil. 1H NMR (400 MHz, CDCl3, 300 K) δ 5.81 (ddt, J 17.1, 10.3, 6.7, 1H), 5.02 (dd, J 17.1, 1.5, 1H), 4.97 (d, J 10.3, 1H), 2.46-2.43 (m, 2H), 2.15 (s, 3H), 2.10-2.05 (m, 2H), 1.65-1.57 (m, 2H), 1.45-1.37 (m, 2H).

후처리

  1. extractionThe aqueous layer was further extracted with EtOAc
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried (Na2SO4)
  4. customEvaporation of the solvent at 30 mbar

출처 및 근거

ORD 기록
ord-35db4e620f934f598ef1d1e024c64282
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314062B2

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