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

HRID 336082ノート

反応式

HRID 336082 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>[CH3:8][O:7][C:6]1[CH2:5][CH2:4][C:3](=[O:9])[C:2]=1[C:12]1[C:13]([CH3:18])=[CH:14][C:15]([CH3:17])=[CH:16][C:11]=1[CH3:10]

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 78.9%

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 (32.3 g 169 mmol), 2,4,6-trimethylphenyl boronic acid (29.5 g, 180 mmol) and freshly ground potassium phosphate (63.7 g) in degassed toluene (800 ml) under N2 is added Pd(OAc)2 (896 mg, 8 mmol) and S-Phos (1.64 g, 4 mmol), and the reaction heated to 90° C. with stirring under N2 overnight. The reaction is partitioned between ethyl acetate (500 ml) and water (500 ml), and the organic layer is removed and the aqueous phase is extracted with ethyl acetate (2×300 ml). The combined organic extracts are evaporated under reduced pressure and the residue is purified to give 3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (30.7 g).

後処理

  1. customThe reaction is partitioned between ethyl acetate (500 ml) and water (500 ml)
  2. customthe organic layer is removed
  3. extractionthe aqueous phase is extracted with ethyl acetate (2×300 ml)
  4. customThe combined organic extracts are evaporated under reduced pressure
  5. customthe residue is purified

出典と根拠

ORDレコード
ord-7dd1b5ee05ca43718b484008c801776e
出典データセット
uspto-grants-2014_11
特許番号
US08889595B2

反応ノート

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