Boron trifluoride etherate → 2-allyl-2-phenyltetrahydro-2H-pyran

HRID 71260

Reaktionsgleichung

Reaktionsgleichung von HRID 71260
[C:1]1([C:7]2(O)[CH2:12][CH2:11][CH2:10][CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([Si](C)(C)C)[CH:15]=[CH2:16].B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:16]([C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)[CH:15]=[CH2:14]

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 69808AllyltrimethylsilaneHCID 145879022-phenyltetrahydro-2H-pyran-2-ol

Produkt 1

HCID 666850742-allyl-2-phenyltetrahydro-2H-pyranAusbeute 78,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-phenyltetrahydro-2H-pyran-2-ol (1.066 g, 5.98 mmol) and allyltrimethylsilane (1.901 mL, 11.96 mmol) in CH2Cl2 (25 mL) at 0° C. was added BF3.OEt2 (0.758 mL, 5.98 mmol) dropwise, and the mixture was stirred at the same temperature for 1 hr. Then the reaction was quenched with saturated NaHCO3 and the product was extracted with EtOAc. The extract was washed with brine, and the combined aqueous layers were back extracted with EtOAc once and combined. The extracts were dried over Na2SO4 and evaporated to give an oily residue. It was purified by Combiflash (80 g silica gel) eluting with 1:9 followed by 4:6 EtOAc-hexane to give 2-allyl-2-phenyltetrahydro-2H-pyran as oil (0.954 g). 1H NMR (400 MHz, CCl3D) δ ppm 7.10-7.45 (5H, m), 5.47-5.65 (1H, m, J=17.19, 10.11, 7.33, 7.33 Hz), 4.84-5.00 (2H, m), 3.64-3.78 (1H, m), 3.41-3.57 (1H, m), 2.35-2.48 (1H, m), 2.20-2.35 (1H, m), 1.55-1.81 (4H, m), 1.35-1.54 (2H, m).

Aufarbeitung

  1. customThen the reaction was quenched with saturated NaHCO3
  2. extractionthe product was extracted with EtOAc
  3. washThe extract was washed with brine
  4. extractionthe combined aqueous layers were back extracted with EtOAc once
  5. dry with materialThe extracts were dried over Na2SO4
  6. customevaporated
  7. customto give an oily residue
  8. customIt was purified by Combiflash (80 g silica gel)
  9. washeluting with 1:9

Quellen und Nachweise

ORD-Eintrag
ord-1a426bcc3fa149da9695a60e0eb0bba4
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822510B2

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