Sodium Acetate → HCID 71114867, 화합물

HRID 1624040노트

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HRID 1624040 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 71114867HCID 71114867, 화합물수율 50%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-67fa1d576c1346b68ad1230482a1c228
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778984B2

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