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

HRID 2261728

반응식

HRID 2261728 반응식
[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]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 10556Isobutyl iodide2회HCID 11430Potassium CarbonateHCID 589173Ethyl 2-(methoxyimino)-4-oxopentanoate

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-83f7b6a6cfc84cdeb6d1a0b0560ad9f0
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07846960B2

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