Hydrochloric Acid → 4,4-Difluoro-1-[4-(morpholino)phenyl]-butane-1,3-dione

HRID 441042

반응식

HRID 441042 반응식
[F:1][CH:2]([F:8])[C:3](OCC)=[O:4].C[O-].[Na+].[O:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24](=[O:26])[CH3:25])=[CH:20][CH:19]=2)[CH2:14][CH2:13]1.Cl>C1COCC1>[F:1][CH:2]([F:8])[C:3](=[O:4])[CH2:25][C:24]([C:21]1[CH:20]=[CH:19][C:18]([N:15]2[CH2:14][CH2:13][O:12][CH2:17][CH2:16]2)=[CH:23][CH:22]=1)=[O:26]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 9961Ethyl difluoroacetateHCID 383624-MorpholinoacetophenoneHCID 10942334Sodium Methoxide

생성물 1

HCID 189203754,4-Difluoro-1-[4-(morpholino)phenyl]-butane-1,3-dione수율 91.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Ethyl difluoroacetate (2.30 g, 18.5 mmol) was placed in a 100 mL round bottom flask and dissolved in THF (25 mL). To the stirred solution was added 25 weight % sodium methoxide (4.90 g, 22.6 mmol) followed by 4'-morpholinoacetophenone (3.45 g, 16.8 mmol). The reaction was stirred at room temperature overnight (15.8 hours), then treated with 3N HCl (13 mL). The reaction was extracted with ethyl acetate (20 mL), washed with brine (20 mL), dried over MgSO4, and concentrated in vacuo to give a green solid (4.36 g) which was recrystallized from methylene chloride/isooctane to give the diketone as a yellow solid (3.27 g, mp 102°-3° C., 69%). 1H NMR (CDCl3) 300 MHz 15.80 (br s, 1H), 7.86 (d, J=9.1 Hz, 2H), 6.90 (d, J=9.1 Hz, 2H), 6.46 (s, 1H), 5.99 (t, J=54.4 Hz, 1H), 3.84 (m,4 H), 3.36 (m, 4H); 19F NMR (CDCl3) 300 MHz: -126.75 (d); M+ 283.

후처리

  1. extractionThe reaction was extracted with ethyl acetate (20 mL)
  2. washwashed with brine (20 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ed01b5ae42db4827a7816770ea28b544
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05521207

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