Hydrochloric Acid → 4,4-Difluoro-1-(4-trifluoromethylphenyl)butane-1,3-dione

HRID 129211

반응식

HRID 129211 반응식
[F:1][CH:2]([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=1.Cl>CCOCC.C1COCC1>[F:8][CH:2]([F:1])[C:3](=[O:5])[CH2:21][C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:13]([F:12])([F:23])[F:24])=[CH:15][CH:16]=1)=[O:22]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 9961Ethyl difluoroacetateHCID 697311-(4-(Trifluoromethyl)phenyl)ethan-1-oneHCID 10942334Sodium Methoxide

생성물 1

HCID 189203694,4-Difluoro-1-(4-trifluoromethylphenyl)butane-1,3-dione수율 91%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

Ethyl difluoroacetate (2.78 g, 22.4 mmol) was placed in a 100 mL round bottom flask and dissolved in ether (10 mL). To the stirred solution was added 25 weight % sodium methoxide (6.02 g, 27.8 mmol) followed by 4'-(trifluoromethyl)acetophenone (3.80 g, 20.2 mmol) and THF (20 mL). The reaction was stirred air room temperature overnight (15.6 hours), then treated with 3N HCl (20 mL). The organic layer was collected and washed with brine, dried over MgSO4, concentrated in vacuo to give a brown oil (4.88 g, 91%). 1H NMR (acetone d6) 300 MHz 15.10 (br s, 1H), 8.03 (d, J=8.7 Hz, 2H), 7.77 (d, J=8.5 Hz, 2H), 6.59 (s, 1H), 6.02 (t, J=54.2 Hz, 1H); 19F NMR (acetone d6) 300 MHz: - 63.70 (s), -127.10 (d); M+266.

후처리

  1. customThe organic layer was collected
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-11b89add7c5f495c92421dde331b43ff
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05466823

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