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

HRID 2075211

Reaktionsgleichung

Reaktionsgleichung von HRID 2075211
[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

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acid2×HCID 12052Triethylsilane2×HCID 584153851-(Benzofuran-5-yl)-1-phenylpropan-1-ol

Produkt 1

HCID 584153565-(1-Phenylpropyl)-benzofuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4e824007acd8468580566e8c952934a3
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919519B2

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