Dimethylformamide dimethyl acetal → HCID 71114823、化合物

HRID 1624053ノート

反応式

HRID 1624053 の反応式
[CH3:1][C:2]1([CH3:18])[CH2:7][CH2:6][CH:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=2[CH3:16])[CH2:4][C:3]1=[O:17].CO[CH:21](OC)[N:22]([CH3:24])[CH3:23]>>[CH3:21][N:22](/[CH:24]=[C:4]1/[CH:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=2[CH3:16])[CH2:6][CH2:7][C:2]([CH3:18])([CH3:1])[C:3]/1=[O:17])[CH3:23]

参加物

3

反応物 2

HCID 78373Dimethylformamide dimethyl acetalHCID 71114867HCID 71114867、化合物

生成物 1

HCID 71114823HCID 71114823、化合物収率 27%

実験手順

4-(4,4-Dimethyl-3-oxo-cyclohexyl)-3-methyl-benzonitrile (0.6 g, 2.49 mmol) in N,N-dimethylformamide dimethylacetal (50 mL) is stirred at 90° C. for two days. The mixture is cooled to room temperature and concentrated in vacuo. The residue is diluted with ethyl acetate (50 mL) and water (50 mL). The organic phase is separated and the aqueous phase is extracted with ethyl acetate (3×50 mL). The combined organic phase is washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue is purified by silica gel flash chromatography, eluting with pet ether:EtOAc 1:1 to MeOH:DCM=1:30 to give 4-[(2Z)-2-(dimethylaminomethylene)-4,4-dimethyl-3-oxo-cyclohexyl]-3-methyl-benzonitrile (0.2 g, 27%).

後処理

  1. concentrationconcentrated in vacuo
  2. additionThe residue is diluted with ethyl acetate (50 mL) and water (50 mL)
  3. customThe organic phase is separated
  4. extractionthe aqueous phase is extracted with ethyl acetate (3×50 mL)
  5. washThe combined organic phase is washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel flash chromatography
  9. washeluting with pet ether:EtOAc 1:1 to MeOH

出典と根拠

ORDレコード
ord-3555c86ad52c47f3971de1e06ea9aa19
出典データセット
uspto-grants-2014_07
特許番号
US08778984B2

反応ノート

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