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

HRID 129208

反応式

HRID 129208 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-e565815ee99745298851848cbd02a839
出典データセット
uspto-grants-1995_11
特許番号
US05466823

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