HCID 58972217, compound → HCID 58972237, compound

HRID 922071Notes

Reaction equation

HRID 922071 reaction equation
C[O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11]C)=[C:5]([CH3:13])[C:4]=1[CH2:14]/[CH:15]=[C:16](\[CH3:25])/[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:24])[CH3:23]>C(C#N)(C)=O.C(Cl)Cl.O>[CH3:25]/[C:16](=[CH:15]\[CH2:14][C:4]1[C:3](=[O:2])[C:8]([CH3:9])=[C:7]([CH3:10])[C:6](=[O:11])[C:5]=1[CH3:13])/[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:24])[CH3:23]

Participants

5

Reactant 1

HCID 58972217HCID 58972217, compound

Product 1

HCID 58972237HCID 58972237, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 694302-OxopropiononitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

Ceric ammonium nitrate (90.1 mg, 0.164 mmol) was dissolved into H2O (0.5 mL) and AcCN (0.5 mL) and cooled to 0° C. A solution containing 25.2 mg N-((E)-7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-5-methylhept-5-enyl)acetamide (0.0725 mmol) in AcCN (1 mL) and CH2Cl2 (0.25 mL) was added over 0.5 min. The reaction was stirred for 0.75 h at 0° C. then diluted with H2O (2 mL). The layers were separated and the organic phase diluted with EtOAc (5 mL) and washed with H2O (3×2 mL). The combined aqueous phase was back extracted using EtOAc (3×4 mL) and discarded. The combined organics were washed with brine (2×3 mL), dried over Na2SO4, concentrated in vacuo and subjected to flash chromatography (SiO2) gave N-((5E)-5-methyl-7-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)hept-5-enyl)acetamide as a bright yellow liquid. 1H NMR (400 MHz, CDCl3) d 5.61 (br s, 1H), 3.20 (m, 4H), 2.01 (m, 14H), 1.72 (s, 3H), 1.41 (m, 2H). 1C NMR (100 MHz, CDCl3) d 187.9, 187.1, 170.0, 143.1, 140.43 140.37, 136.7, 119.9, 60.1, 39.5, 39.2, 29.1, 25.6, 25.0, 23.3, 16.1, 12.4, 12.2.

Workup

  1. additionwas added over 0.5 min
  2. customThe layers were separated
  3. additionthe organic phase diluted with EtOAc (5 mL)
  4. washwashed with H2O (3×2 mL)
  5. extractionThe combined aqueous phase was back extracted
  6. washThe combined organics were washed with brine (2×3 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e1f7b26cb1c476ebf6e5a9ebdf20be1
Source dataset
uspto-grants-2016_03
Patent number
US09278085B2

Reaction notes

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