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

HRID 495183노트

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HRID 495183 반응식
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

참가 물질

5

반응물 2

HCID 11776Triphenylphosphine2회HCID 86610520Methyl 3,5-diallyloxy-2-benzoyl-6-ethylphenylacetate

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매2회HCID 176Acetic Acid용매

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온도
80 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-3d35b8883e314912a6f294d42a3a62b8
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538224B2

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