Hydrochloric Acid → 4,4-Difluoro-1-[2-cyclohexenyl]-butane-1,3-dione

HRID 129208

반응식

HRID 129208 반응식
[F:1][CH:2]([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].[C:12]([C:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=1)(=[O:14])[CH3:13].Cl>CCOCC>[F:8][CH:2]([F:1])[C:3](=[O:5])[CH2:13][C:12]([CH:15]1[CH2:20][CH2:19][CH2:18][CH:17]=[CH:16]1)=[O:14]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 9961Ethyl difluoroacetateHCID 136121-AcetylcyclohexeneHCID 10942334Sodium Methoxide

생성물 1

HCID 189203604,4-Difluoro-1-[2-cyclohexenyl]-butane-1,3-dione수율 94.3%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

Ethyl difluoroacetate (4.71 g; 38 mmol) was placed in a 100 mL round bottom flask and dissolved in ether (20 mL). To the stirred solution was added 25 weight % sodium methoxide (9.68 g, 45 mmol) followed by 1-acetyl-1-cyclohexene(4.27 g, 34 mmol). The reaction was stirred at room temperature overnight (17.5 hours), then treated with 3N HCl (20 mL). The organic layer was collected and washed with brine (20 mL), dried over MgSO4, and concentrated in vacuo to give a brown oil (6.48 g, 93%). 1H NMR (CDCl3) 300 MHz 15.00 (br s, 1H), 6.09 (s, 1H), 5.92 (t, J=54.4 Hz,1H), 2.31 (m, 4H), 1.64 (m, 4H); 19F NMR (CDCl3) 300 MHz: -126.94; M+202.

후처리

  1. customThe organic layer was collected
  2. washwashed with brine (20 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e565815ee99745298851848cbd02a839
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05466823

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