Hydrochloric Acid → 3-[4-(5-Methoxycarbonyl-1-pentenyl)phenyl]isoxazole-4-carboxylic acid

HRID 2111026노트

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HRID 2111026 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1.[C:16]([O:23][CH3:24])(=[O:22])[CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Cl>O1CCOCC1.C(N(CC)C(C)C)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:24][O:23][C:16]([CH2:17][CH2:18][CH2:19][CH:20]=[CH:21][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1)=[O:22]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 80271Tri-o-tolylphosphineHCID 520082Methyl 5-HexenoateHCID 688807933-(4-Iodophenyl)isoxazole-4-carboxylic acid

생성물 1

HCID 688844633-[4-(5-Methoxycarbonyl-1-pentenyl)phenyl]isoxazole-4-carboxylic acid수율 79.3%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매HCID 521913N,N-Diethyl-2-propanamine용매

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온도
100 °C

실험 절차

3-(4-Iodophenyl)isoxazole-4-carboxylic acid (315 mg, 1.0 mmol) was dissolved in a mixed solvent of 1,4-dioxane (5 ml) and diethylisopropylamine (2.5 ml), methyl 5-hexenoate (179 mg, 1.4 mmol), tri-(o-tolyl)phosphine (122 mg, 0.4 mmol) and palladium acetate (22.4 mg, 0.1 mmol) were added, and the mixture was stirred overnight at 100° C. 1N Hydrochloric acid was added, and the mixture was extracted once with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane:ethyl acetate=7:3-6:4) to give the title compound (250 mg, 79%).

후처리

  1. additionwere added
  2. extractionthe mixture was extracted once with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel chromatography (hexane:ethyl acetate=7:3-6:4)

출처 및 근거

ORD 기록
ord-c9e8ac7102724a18ab02e2e4362b260d
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517996B2

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