Ammonium Chloride → 7-Octen-2-one

HRID 1879245ノート

反応式

HRID 1879245 の反応式
[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]

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 46703846N-methoxy-N-methylhept-6-enamideHCID 178418573HCID 178418573、化合物

生成物 1

HCID 193157-Octen-2-one収率 96%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-35db4e620f934f598ef1d1e024c64282
出典データセット
uspto-grants-2012_11
特許番号
US08314062B2

反応ノート

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