Hydroxyamine chloride → methyl (E)-2-[2-[[4-[(E)-C-ethyl-N-hydroxycarbonimidoyl]-2,5-dimethylphenoxy]methyl]phenyl]-3-methoxyprop-2-enoate

HRID 1619160노트

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HRID 1619160 반응식
[CH3:1][C:2]1[CH:23]=[C:22]([C:24](=O)[CH2:25][CH3:26])[C:21]([CH3:28])=[CH:20][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1/[C:12](=[CH:17]\[O:18][CH3:19])/[C:13]([O:15][CH3:16])=[O:14].[Cl-].[NH2:30][OH:31]>CO>[OH:31]/[N:30]=[C:24](/[C:22]1[C:21]([CH3:28])=[CH:20][C:3]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2/[C:12](=[CH:17]\[O:18][CH3:19])/[C:13]([O:15][CH3:16])=[O:14])=[C:2]([CH3:1])[CH:23]=1)\[CH2:25][CH3:26]

참가 물질

4

반응물 2

HCID 21878317Hydroxyamine chlorideHCID 67955272(E)-methyl 2-(2-((2,5-dimethyl-4-propionylphenoxy)methyl)phenyl)-3-methoxyacrylate

생성물 1

HCID 88531482methyl (E)-2-[2-[[4-[(E)-C-ethyl-N-hydroxycarbonimidoyl]-2,5-dimethylphenoxy]methyl]phenyl]-3-methoxyprop-2-enoate수율 67%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 0.17 g (0.44 mmol) of (E)-methyl 2-(2-((2,5-dimethyl-4-propionylphenoxy)methyl)phenyl)-3-methoxyacrylate obtained in Step 3 and 0.06 g (0.88 mmol) of hydroxylamine chloride in 10 mL of methanol was added 0.8 g of a molecular sieve for dehydration. The reaction mixture was stirred at room temperature for 3 hours and filtered through celite and the filtrate was concentrated in a vacuum. The concentrate was stirred in water (10 mL) and extracted twice with 10 mL of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified through silica gel chromatography to produce (E)-methyl 2-(2-((4-((E)-1-(hydroxyimino)propyl)-2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylate as a white solid (0.11 g, yield: 67%).

후처리

  1. filtrationfiltered through celite
  2. concentrationthe filtrate was concentrated in a vacuum
  3. stirringThe concentrate was stirred in water (10 mL)
  4. extractionextracted twice with 10 mL of dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationfollowed by vacuum concentration
  7. customThe residue was purified through silica gel chromatography

출처 및 근거

ORD 기록
ord-5cfcd446b09d4d2ba82fbe30b9248f18
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772290B2

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