Acetone → 6-fluoro-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

HRID 1911261

반응식

HRID 1911261 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH3:12][C:13](=O)[CH3:14].N1CCCC1.CCOC(C)=O>CO>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][C:13]([CH3:14])([CH3:12])[CH2:9][C:8]2=[O:10]

참가 물질

6

반응물 4

HCID 180AcetoneHCID 8857Ethyl AcetateHCID 31268PyrrolidineHCID 959922-Acetyl-4-fluorophenol

생성물 1

HCID 110632936-fluoro-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one수율 56.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

In a 500 mL round-bottomed flask was added 1-(5-fluoro-2-hydroxyphenyl)ethanone (20.0 g, 130 mmol, Aldrich Chemical), propan-2-one (19.0 mL, 260 mmol), and pyrrolidine (21.5 mL, 260 mmol) in methanol (150 mL) to give a orange solution. The reaction mixture was stirred at ambient temperature for 48 h. The reaction mixture was poured into EtOAc (200 mL) and washed with 1N HCl (50 mL), saturated NaHCO3 (50 mL), and brine (50 mL). The organic portion was dried (Na2SO4), filtered, and concentrated to provide an orange residue which was purified by silica gel chromatography (gradient elution, 0-20% EtOAc/hexanes) to provide the title compound (14.2 g, 73.1 mmol, 56%) as a white solid. MS (DCI/NH3) m/z 208 (M+NH4)+.

후처리

  1. customto give a orange solution
  2. washwashed with 1N HCl (50 mL), saturated NaHCO3 (50 mL), and brine (50 mL)
  3. dry with materialThe organic portion was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide an orange residue which
  7. customwas purified by silica gel chromatography (gradient elution, 0-20% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-19c5157fa79d485f998e9cf4f9ec781c
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604053B2

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