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

HRID 71260

반응식

HRID 71260 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 666850742-allyl-2-phenyltetrahydro-2H-pyran수율 78.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1a426bcc3fa149da9695a60e0eb0bba4
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822510B2

연결된 노트

불러오는 중…