Boron trifluoride etherate → 2-Benzhydryl-2H-pyran-4(3H)-one

HRID 909704

반응식

HRID 909704 반응식
B(F)(F)F.CCOCC.[CH3:10][O:11]/[CH:12]=[CH:13]/[C:14]([O:16][Si](C)(C)C)=[CH2:15].[C:21]1([CH:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)C=O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CCOCC>[CH:27]([CH:10]1[CH2:15][C:14](=[O:16])[CH:13]=[CH:12][O:11]1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 13696DiphenylacetaldehydeHCID 5366448trans-1-Methoxy-3-trimethylsilyloxy-1,3-butadiene

생성물 1

HCID 666308482-Benzhydryl-2H-pyran-4(3H)-one수율 80.4%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
-78 °C

실험 절차

A solution of boron trifluoride diethyl etherate (7.8 g, 55 mmol) in dry ether (50 ml) was added to a stirred mixture of E-1-methoxy-3-trimethylsilyloxybuta-1,3-diene (8.3 g, 48 mmol), diphenylacetaldehyde 1 (11.4 g, 58 mmol) and dry ether (300 ml) cooled to −78° C. After one hour, the mixture was allowed to reach 0° C. for three hours. The deep red reaction mixture was quenched with saturated aqueous NaHCO3, and the mixture was allowed to come to room temperature. The organic phase was separated and the aqueous phase was extracted with ether (3×70 ml). The combined organic phases were washed with brine, and dried over anhydrous Na2SO4. Evaporation of solvent under reduced pressure and purification of the crude product by chromatography (hexane/ethyl acetate 8:2) gave 2-diphenylmethyl-2,3-dihydro-4H-pyran-4-one 2 (10.2 g, 80.2%, yield) as a yellow solid.

후처리

  1. waitto reach 0° C. for three hours
  2. customThe deep red reaction mixture
  3. customwas quenched with saturated aqueous NaHCO3
  4. customto come to room temperature
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted with ether (3×70 ml)
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. customEvaporation of solvent
  10. customunder reduced pressure and purification of the crude product by chromatography (hexane/ethyl acetate 8:2)

출처 및 근거

ORD 기록
ord-386e9643c099405695d63c995f045d1c
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017791B2

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