Benzofuran-5-yl(phenyl)methanone → 1-(Benzofuran-5-yl)-1-phenylpropan-1-ol

HRID 2075210

반응식

HRID 2075210 반응식
[CH2:1]([Mg]Cl)[CH3:2].[O:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:15])=[CH:13][C:8]=2[CH:7]=[CH:6]1>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[O:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)([OH:15])[CH2:1][CH3:2])=[CH:13][C:8]=2[CH:7]=[CH:6]1

참가 물질

5

반응물 2

HCID 58415352Benzofuran-5-yl(phenyl)methanoneHCID 178461633HCID 178461633, 화합물

생성물 1

HCID 584153851-(Benzofuran-5-yl)-1-phenylpropan-1-ol

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethylmagnesium chloride (2M in tetrahydrofuran, 10.63 mL, 21.26 mmol) under nitrogen at room temperature was added zinc chloride (0.5M in tetrahydrofuran, 5.67 mL, 2.84 mmol) via syringe. The mixture was stirred at room temperature for 1 h. The reaction mixture was brought to 0° C. and benzofuran-5-yl(phenyl)methanone (3.15 g, 14.17 mmol) in tetrahydrofuran (10 mL) was added via syringe. The reaction mixture was stirred at 0° C. for 2.5 h. The reaction mixture was cooled to room temperature and quenched with saturated aqueous NH4Cl. EtOAc was added, and the aqueous layer was separated and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), and concentrated to give a crude oil. The crude product was purified by silica flash chromatography (0-100% DCM/hexanes) to give 1-(benzofuran-5-yl)-1-phenylpropan-1-ol as an off-white oil. 1H NMR (400 MHz, Chloroform-d) δ ppm 7.69 (1H, d, J=1.6 Hz), 7.60 (1H, d, J=2.2 Hz), 7.39-7.45 (3H, m), 7.28-7.34 (3H, m), 7.22 (1H, tt, J=7.2, 1.4 Hz), 6.73 (1H, dd, J=2.2, 1.0 Hz), 2.38 (2H, q, J=7.3 Hz), 2.09 (1H, s), 0.90 (3H, t, J=7.3 Hz).

후처리

  1. customwas brought to 0° C.
  2. stirringThe reaction mixture was stirred at 0° C. for 2.5 h
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customquenched with saturated aqueous NH4Cl
  5. additionEtOAc was added
  6. customthe aqueous layer was separated
  7. extractionextracted with EtOAc (2×)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customto give a crude oil
  12. customThe crude product was purified by silica flash chromatography (0-100% DCM/hexanes)

출처 및 근거

ORD 기록
ord-b7028cafcc42458a872699eeec107a1a
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919519B2

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