Trifluoroacetic acid → 5-(1-Phenylpropyl)-benzofuran

HRID 2075211

반응식

HRID 2075211 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(O)[CH2:11][CH3:12])=[CH:9][C:4]=2[CH:3]=[CH:2]1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:14]1([CH:10]([C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH:2]=[CH:3][C:4]=3[CH:9]=2)[CH2:11][CH3:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acid2회HCID 12052Triethylsilane2회HCID 584153851-(Benzofuran-5-yl)-1-phenylpropan-1-ol

생성물 1

HCID 584153565-(1-Phenylpropyl)-benzofuran

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a stirred solution of 1-(benzofuran-5-yl)-1-phenylpropan-1-ol (3.14 g, 12.4 mmol) and triethylsilane (2.39 mL, 14.9 mmol) in DCM (10 mL) under nitrogen at 0° C. was added trifluoroacetic acid (4.62 mL, 62.2 mmol) dropwise via syringe. The reaction mixture was stirred at 0° C. for 3 h. Additional triethylsilane (2.39 mL, 14.9 mmol) followed by trifluoroacetic acid (4.62 mL, 62.2 mmol) were added via syringe, and the reaction was brought to room temperature and stirred for 2 h. The reaction mixture was quenched with 1M aqueous NaOH. DCM was added, and the aqueous layer was separated and extracted again with DCM. The combined organic layers were dried (MgSO4) and concentrated to give a crude oil. The crude product was purified by silica flash chromatography to give 5-(1-phenylpropyl)-benzofuran as a transparent oil. MS (ESI) m/z: Calculated: 236.1; Observed: 237.2 (M++1).

후처리

  1. additionwere added via syringe
  2. customwas brought to room temperature
  3. stirringstirred for 2 h
  4. customThe reaction mixture was quenched with 1M aqueous NaOH
  5. additionDCM was added
  6. customthe aqueous layer was separated
  7. extractionextracted again with DCM
  8. dry with materialThe combined organic layers were dried (MgSO4)
  9. concentrationconcentrated
  10. customto give a crude oil
  11. customThe crude product was purified by silica flash chromatography

출처 및 근거

ORD 기록
ord-4e824007acd8468580566e8c952934a3
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919519B2

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