HCID 15137055, compound → HCID 15137057, compound

HRID 527629Notes

Reaction equation

HRID 527629 reaction equation
CC(=C)C[O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9]>CN1CCCC1=O.O>[OH:4][C:5]1[C:6]([CH2:8][C:7]([CH3:12])=[CH2:6])=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 1

HCID 15137055HCID 15137055, compound2×

Product 1

HCID 15137057HCID 15137057, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

Methyl 3-(2-methylallyloxy)benzoate (Intermediate 167, 1.100 g, 5.3 mmol) was dissolved in 1-Methyl-2-pyrrolidinone (12 ml) and heated to 200° C. The solution was stirred for 30 h at the same temperature. After cooling, the mixture was diluted with water and extracted with ethyl acetate. Organic phase was dried over Na2SO4 and evaporated in vacuo to afford a crude product that was purified via Biotage SP1 with Cyclohexane/EtOAc as eluents (from 10/0 to 7/3 for 12 CV, 50 g SNAP Silica column). Fractions were collected and evaporated to afford the title compound (507 mg).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialOrganic phase was dried over Na2SO4
  4. customevaporated in vacuo
  5. customto afford a crude product that
  6. customwas purified via Biotage SP1 with Cyclohexane/EtOAc as eluents (from 10/0 to 7/3 for 12 CV, 50 g SNAP Silica column)
  7. customFractions were collected
  8. customevaporated

Sources & evidence

ORD record
ord-525e106d2c83498b814ef62fb856ab4c
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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