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

HRID 1453066ノート

反応式

HRID 1453066 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.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[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

6

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 2

HCID 178418476HCID 178418476、化合物触媒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%). 1H NMR (CDCl3): δ ?1.17 (t, 3H, J=7.6 Hz), 1.54-1.80 (m, 9H), 1.17 (q, 2H, J=7.6 Hz), 2.73 (m, 2H), 2.84 (m, 2H), 3.80 (s, 3H), 6.75 (d, 1H, J=8.0 Hz), 6.97 (m, 2H).

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-947f42e515c34f5c8698bb4500339625
出典データセット
uspto-grants-2009_01
特許番号
US07473790B2

反応ノート

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