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

HRID 509156ノート

反応式

HRID 509156 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl触媒HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-322cfeffc88d47a0b5314d424c032dea
出典データセット
uspto-grants-2015_08
特許番号
US09096560B2

反応ノート

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