Triphenylphosphine → Methyl 2-benzoyl-6-ethyl-3,5-dihydroxy-phenylacetate

HRID 495183ノート

反応式

HRID 495183 の反応式
C([O:4][C:5]1[C:6]([C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:7]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:8]([CH2:15][CH3:16])=[C:9]([O:11]CC=C)[CH:10]=1)C=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:22]([C:6]1[C:5]([OH:4])=[CH:10][C:9]([OH:11])=[C:8]([CH2:15][CH3:16])[C:7]=1[CH2:17][C:18]([O:20][CH3:21])=[O:19])(=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

参加物

5

反応物 2

HCID 11776Triphenylphosphine2 回HCID 86610520Methyl 3,5-diallyloxy-2-benzoyl-6-ethylphenylacetate

生成物 1

HCID 11995674Methyl 2-benzoyl-6-ethyl-3,5-dihydroxy-phenylacetate収率 101.6%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒2 回HCID 176Acetic Acid溶媒

反応条件

温度
80 °C

実験手順

Methyl 3,5-diallyloxy-2-benzoyl-6-ethylphenylacetate (0.29 g, 0.72 mmol) obtained in Example 5, Step 4 was dissolved in acetic acid (5.0 mL) in an atmosphere of argon. To the solution were added triphenylphosphine (74 mg, 0.28 mmol) and palladium (II) acetate (16 mg, 0.071 mmol), followed by stirring at 80° C. for 5 hours. To the reaction mixture were further added triphenylphosphine (0.15 g, 0.57 mmol) and palladium (II) acetate (32 mg, 0.14 mmol), followed by stirring at 100° C. for 13 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-3/1) to obtain Compound 5 (0.23 g, 60%).

後処理

  1. stirringby stirring at 100° C. for 13 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/9-3/1)

出典と根拠

ORDレコード
ord-3d35b8883e314912a6f294d42a3a62b8
出典データセット
uspto-grants-2009_05
特許番号
US07538224B2

反応ノート

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