Hydrochloric Acid → 3-Acetyl-2-methoxyimino-5-methyl-hexanoic acid ethyl ester

HRID 2261728

反応式

HRID 2261728 の反応式
[CH2:1]([O:3][C:4](=[O:13])[C:5](=[N:10][O:11][CH3:12])[CH2:6][C:7](=[O:9])[CH3:8])[CH3:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:21][CH:22]([CH3:24])[CH3:23].Cl>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:13])[C:5](=[N:10][O:11][CH3:12])[CH:6]([C:7](=[O:9])[CH3:8])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH3:2]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 10556Isobutyl iodide2 回HCID 11430Potassium CarbonateHCID 589173Ethyl 2-(methoxyimino)-4-oxopentanoate

生成物 1

HCID 765400763-Acetyl-2-methoxyimino-5-methyl-hexanoic acid ethyl ester収率 29.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-methoxyimino-4-oxo-pentanoic acid ethyl ester (2.62 g, 14 mmol) in DMF (30 mL) is added potassium carbonate (2.5 g, 18.2 mmol) followed by 1-iodo-2-methyl-propane (1.62 mL, 14 mmol) and the mixture is stirred at ambient temperature overnight. Additional 1-iodo-2-methyl-propane (0.8 mL, 7 mmol) is added and the mixture is stirred at 60° C. for 1 hour. The reaction mixture is diluted with EtOAc and is adjusted to pH 3 with 1N HCl. The organic layer is washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue is purified by column chromatography (0 to 20% EtOAc in hexanes) to give the title compound as a colorless oil (1 g, 29%). 1H NMR (400 MHz, CDCl3) δ 4.33 (q, 2H), 4.06 (s, 3H), 4.03 (dd, 1H), 2.07 (s, 3H), 1.88 (m, 1H), 1.58 (m, 1H), 1.43 (m, 1H), 1.37 (t, 3H), 0.89 (d, 6H).

後処理

  1. stirringthe mixture is stirred at 60° C. for 1 hour
  2. washThe organic layer is washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by column chromatography (0 to 20% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-83f7b6a6cfc84cdeb6d1a0b0560ad9f0
出典データセット
uspto-grants-2010_12
特許番号
US07846960B2

関連ノート

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