Sodium Acetate → HCID 71114867、化合物

HRID 1624040ノート

反応式

HRID 1624040 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[C:5]([CH3:12])[CH:4]=1)#[N:2].[CH3:13][C:14]1([CH3:21])[C:19](=[O:20])[CH:18]=[CH:17][CH2:16][CH2:15]1.C([O-])(=O)C.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)(=O)C>[CH3:13][C:14]1([CH3:21])[CH2:15][CH2:16][CH:17]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[CH3:12])[CH2:18][C:19]1=[O:20]

参加物

6

反応物 3

HCID 517045Sodium AcetateHCID 117883026,6-Dimethyl-2-cyclohexen-1-oneHCID 16218401(4-Cyano-2-methyl-phenyl)boronic acid

生成物 1

HCID 71114867HCID 71114867、化合物収率 50%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 176Acetic Acid溶媒

実験手順

4-Cyano-2-methylphenylboronic acid (0.81 g, 5 mmol), 6,6-dimethylcyclohex-2-enone (Canadian Journal of Chemistry, 1981, 59, 2096-2115) (0.55 g, 5 mmol), SbCl3 (0.11 g, 0.5 mmol), sodium acetate (0.82 g, 10 mmol), and palladium acetate (0.11 g, 0.5 mmol) are added to acetic acid (30 mL) under an atmosphere of argon. The reaction mixture is stirred at room temperature for three days. The mixture is filtered and the filtrate is poured into water (150 mL). The organic phase is separated and the aqueous phase is extracted with ethyl acetate (3×100 mL). The combined organic layers are washed with saturated sodium bicarbonate solution (3×100 mL), brine (3×50 mL), dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue is purified by silica gel column chromatography eluting with pet ether: EtOAc=10:1 to give the title compound as a light yellow solid (0.6 g, 50%). GC/MS 241 (M+1).

後処理

  1. filtrationThe mixture is filtered
  2. additionthe filtrate is poured into water (150 mL)
  3. customThe organic phase is separated
  4. extractionthe aqueous phase is extracted with ethyl acetate (3×100 mL)
  5. washThe combined organic layers are washed with saturated sodium bicarbonate solution (3×100 mL), brine (3×50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel column chromatography
  9. washeluting with pet ether

出典と根拠

ORDレコード
ord-67fa1d576c1346b68ad1230482a1c228
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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