Potassium Phosphate, Tribasic → 2-(2,4,6-Trimethylphenyl)-3-methoxy-cyclopent-2-enone

HRID 509156

반응식

HRID 509156 반응식
Br[C:2]1[C:3](=[O:9])[CH2:4][CH2:5][C:6]=1[O:7][CH3:8].[CH3:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>[CH3:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[C:2]1[C:3](=[O:9])[CH2:4][CH2:5][C:6]=1[O:7][CH3:8]

참가 물질

7

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 2921842,4,6-Trimethylbenzeneboronic acidHCID 110954262-Bromo-3-methoxycyclopent-2-enone

생성물 1

HCID 155776462-(2,4,6-Trimethylphenyl)-3-methoxy-cyclopent-2-enone수율 76.3%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl촉매HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

To a suspension of 2-bromo-3-methoxy-cyclopent-2-enone (6.75 g, 35.3 mmol), 2,4,6-trimethylphenyl boronic acid (6.99 g, 42.6 mmol) and freshly ground potassium phosphate (15 g, 70.6 mmol) in degassed toluene (180 ml) under nitrogen are added Pd(OAc)2 (159 mg, 0.71 mmol) and S-Phos (579 mg, 1.41 mmol), and the reaction heated to 90° C. with stirring under N2 for 4 hours. The reaction mixture is partitioned between ethyl acetate (150 ml) and water (150 ml), and the organic layer is removed, Silica gel is added to the organic layer, the solvent is evaporated under reduced pressure and the residue is purified by flash chromatography on silica gel to give 2-(2,4,6-trimethylphenyl)-3-methoxy-cyclopent-2-enone (6.2 g).

후처리

  1. customThe reaction mixture is partitioned between ethyl acetate (150 ml) and water (150 ml)
  2. customthe organic layer is removed
  3. additionSilica gel is added to the organic layer
  4. customthe solvent is evaporated under reduced pressure
  5. customthe residue is purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-322cfeffc88d47a0b5314d424c032dea
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096560B2

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