Dihydrocoumarin → HCID 23505057, compound

HRID 1885020Notes

Reaction equation

HRID 1885020 reaction equation
[O:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:2]1=[O:3].[CH2:12]([NH:15][CH2:16][CH:17]=[CH2:18])[CH:13]=[CH2:14]>C1(C)C=CC=CC=1>[CH2:12]([N:15]([CH2:16][CH:17]=[CH2:18])[C:2](=[O:3])[CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[OH:1])[CH:13]=[CH2:14]

Participants

4

Reactant 2

HCID 660DihydrocoumarinHCID 31279Diallylamine

Product 1

HCID 23505057HCID 23505057, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

19.5 g of dihydrocoumarine was placed in a 250 ml round bottom flask with 20 ml of diallyl amine and 60 ml of toluene. The reaction mixture was stirred for 6 hrs at 50° C. The reaction mixture was then cooled, concentrated, and extracted with ethyl acetate and water. The organic phase was collected and concentrated to obtain dried solid. The obtained solid was recrystallized with ethyl acetate/n-hexane, filtered, washed with n-hexane, and vacuumed to dryness. 17.2 g of the product of formula (VIII) was obtained.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate and water
  4. customThe organic phase was collected
  5. concentrationconcentrated
  6. customto obtain
  7. customdried solid
  8. customThe obtained solid was recrystallized with ethyl acetate/n-hexane
  9. filtrationfiltered
  10. washwashed with n-hexane

Sources & evidence

ORD record
ord-ebeedc022cb748b6896bf3e76369e7c4
Source dataset
uspto-grants-2004_07
Patent number
US06767970B2

Reaction notes

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