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

HRID 2111026ノート

反応式

HRID 2111026 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒HCID 521913N,N-Diethyl-2-propanamine溶媒

反応条件

温度
100 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-c9e8ac7102724a18ab02e2e4362b260d
出典データセット
uspto-grants-2009_04
特許番号
US07517996B2

反応ノート

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