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

HRID 1352202노트

반응식

HRID 1352202 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-2e24334c459c46f6a89d408fe879391b
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07220734B2

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