Tricyclohexylphosphine → 2,3-Dihydro-5-[4-(phenylmethoxy)phenyl]-1H-inden-1-one

HRID 1352202ノート

反応式

HRID 1352202 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[C:24](=[O:28])[CH2:23][CH2:22]2.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[F-].[K+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[C:24](=[O:28])[CH2:23][CH2:22]3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 75806TricyclohexylphosphineHCID 5206955-Bromo-1-indanoneHCID 522689Potassium FluorideHCID 27343144-Benzyloxy-phenylboronic acid

生成物 1

HCID 211000302,3-Dihydro-5-[4-(phenylmethoxy)phenyl]-1H-inden-1-one収率 36.1%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of 4-benzyloxyphenyl boronic acid (0.15 g, 0.66 mmol), 5-bromo-1-indanone (0.10 g, 0.44 mmol), palladium acetate (2.0 mg, 0.009 mmol), tricyclohexylphosphine (7.0 mg, 0.018 mmol) and potassium fluoride (0.077 g, 1.32 mmol) in dioxane (2.5 mL) was stirred at 75° C. for 3 h. The reaction mixture was filtered through celite. Silica gel chromatography eluting with 25% ethyl acetate/hexane gave 0.05 g of desired product: 1H NMR (500 MHz, CDCl3) δ 7.85 (d, J=8.0 Hz, 1H), 7.68 (s, 1H), 7.62 (t, 3H), 7.51 (d, J=7.3 Hz, 2H), 7.46 (t, J=7.5 Hz, 2H), 7.38–7.42 (m, 1H), 7.13 (d, J=8.7 Hz, 2H), 5.18 (s, 2H), 3.23 (t, J=5.8 Hz, 2H), 2.78 (t, J=6.0 Hz, 2H).

後処理

  1. filtrationThe reaction mixture was filtered through celite
  2. washSilica gel chromatography eluting with 25% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-2e24334c459c46f6a89d408fe879391b
出典データセット
uspto-grants-2007_05
特許番号
US07220734B2

反応ノート

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