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

HRID 129207

反応式

HRID 129207 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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,4H), 3.36 (m, 4H); 19F NMR (CDCl3) 300 MHz: -126.75 (d); M+283.

後処理

  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

出典と根拠

ORDレコード
ord-c140a6e036c340d58d3000033e28f887
出典データセット
uspto-grants-1995_11
特許番号
US05466823

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