1-Cyclopentyl-2-propen-1-ol → 1-Cyclopentyl-3-(3-ethyl-4-methoxy-phenyl)-propan-1-one

HRID 858617ノート

反応式

HRID 858617 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH2:10][CH3:11])[CH:3]=1.[CH:12]1([CH:17]([OH:20])[CH:18]=[CH2:19])[CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[CH:12]1([C:17](=[O:20])[CH2:18][CH2:19][C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH2:10][CH3:11])[CH:3]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

参加物

5

反応物 3

HCID 1451331-Cyclopentyl-2-propen-1-olHCID 516892Sodium BicarbonateHCID 133016024-Bromo-2-ethyl-1-methoxybenzene

生成物 1

HCID 587625321-Cyclopentyl-3-(3-ethyl-4-methoxy-phenyl)-propan-1-one収率 47.2%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
140 °C

実験手順

A mixture of bromide (1.3 g, 6.02 mmol, from step 1), 1-Cyclopentyl-2-propen-1-ol (1.14 g, 9.07 mmol), dichlorobis (triphenylphosphine) palladium (II) (85 mg, 0.12 mmol), sodium bicarbonate (0.61 g, 7.25 mmol) in N-methylpyrrolidinone (12 mL) was heated to 140° C. under N2 for 5 h. The reaction mixture was partitioned between 1N HCl and EtOAc. The organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated to a brown oil. The oil was purifed by silica gel chromatography to give the title compound as a yellow oil (0.74 g, 47%).

後処理

  1. customThe reaction mixture was partitioned between 1N HCl and EtOAc
  2. washThe organic layer was washed with saturated NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a brown oil

出典と根拠

ORDレコード
ord-432d4d27936943368dd1080eddbad11b
出典データセット
uspto-grants-2006_12
特許番号
US07148226B2

反応ノート

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