4-Hydroxybenzoic Acid → 4-(3-Methyl-1,2,4-oxadiazol-5-yl)phenol

HRID 423274

反応式

HRID 423274 の反応式
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C([N:18]1[CH:22]=[CH:21]N=C1)(N1C=CN=C1)=O.O[NH:24]C(=O)C>C(OCC)(=O)C.C1COCC1.C1(C)C=CC=CC=1>[CH3:21][C:22]1[N:18]=[C:6]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:10][CH:9]=2)[O:8][N:24]=1

参加物

7

反応物 3

HCID 1354-Hydroxybenzoic AcidHCID 1990Acetohydroxamic AcidHCID 682631,1'-Carbonyldiimidazole

生成物 1

HCID 36924074-(3-Methyl-1,2,4-oxadiazol-5-yl)phenol収率 10.3%

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a mixed solution of 4-hydroxybenzoic acid (1.0 g) in a mixed solution (15 mL) of toluene and THF (toluene:THF=2:1, v/v) was added carbonyldiimidazole (1.29 g), and the mixture was stirred at room temperature for 1 hour. Subsequently, N-hydroxyacetamide (644 mg) was added thereto, and the mixture was further heated at 150° C. for 2 hours under reflux. The reaction solution was allowed to stand for cooling down to room temperature, diluted with ethyl acetate, washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1, v/v) to give the title compound (132 mg).

後処理

  1. temperaturethe mixture was further heated at 150° C. for 2 hours
  2. temperatureunder reflux
  3. temperaturefor cooling down to room temperature
  4. washwashed successively with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (ethyl acetate

出典と根拠

ORDレコード
ord-5f29a971bc74401da4bee98c45b8b125
出典データセット
uspto-grants-2012_01
特許番号
US08101774B2

関連ノート

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