Methanol → HCID 10753499, compound

HRID 1383424Notes

Reaction equation

HRID 1383424 reaction equation
[C:1]([C:3]1[C:4](=[O:19])[O:5][C:6]2[C:11]([C:12]=1[CH3:13])=[CH:10][CH:9]=[C:8]([O:14]CC=C)[C:7]=2[CH3:18])#[N:2].CO.C(N(CC)[C:25]1[CH:30]=CC=C[CH:26]=1)C>>[C:1]([C:3]1[C:4](=[O:19])[O:5][C:6]2[C:11]([C:12]=1[CH3:13])=[CH:10][C:9]([CH2:30][CH:25]=[CH2:26])=[C:8]([OH:14])[C:7]=2[CH3:18])#[N:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 7061N,N-DiethylanilineHCID 10658656HCID 10658656, compound

Product 1

HCID 10753499HCID 10753499, compoundYield 76%

Procedure

A solution of 3-cyano-4,8-dimethyl-7-allyloxycoumarin (1.27 g, 4.97 mmoles) in 14 mL of N,N-diethylaniline was deoxygenated with argon for 30 minutes, and then was heated at reflux for 6 hours, while being purged by bubbling argon through the solution. The reaction mixture was chilled in ice, the resulting precipitate was collected by suction filtration and dried in vacuo. Recrystallisation from a mixture of benzene:methanol gave 0.97 g (76% yield) of 3-cyano-4,8-dimethyl-6-allyl-7-hydroxycoumarin (3, R═CN, R′=H) as a pale brown solid: mp 234-235° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. customwhile being purged
  4. customby bubbling argon through the solution
  5. temperatureThe reaction mixture was chilled in ice
  6. filtrationthe resulting precipitate was collected by suction filtration
  7. customdried in vacuo
  8. customRecrystallisation
  9. additionfrom a mixture of benzene

Sources & evidence

ORD record
ord-a037b608380b471e8196bdf9b75c1874
Source dataset
uspto-grants-2001_07
Patent number
US06255324B1

Reaction notes

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