Water → HCID 10824427, compound

HRID 1383427Notes

Reaction equation

HRID 1383427 reaction equation
[F:1][C:2]1[C:3](=[O:18])[O:4][C:5]2[C:10]([C:11]=1[CH3:12])=[CH:9][CH:8]=[C:7]([O:13]CC=C)[C:6]=2[CH3:17].O.C(N(CC)[C:23]1[CH:28]=CC=C[CH:24]=1)C>>[F:1][C:2]1[C:3](=[O:18])[O:4][C:5]2[C:10]([C:11]=1[CH3:12])=[CH:9][C:8]([CH2:28][CH:23]=[CH2:24])=[C:7]([OH:13])[C:6]=2[CH3:17]

Participants

4

Reactant 3

HCID 962WaterHCID 7061N,N-DiethylanilineHCID 21857121HCID 21857121, compound

Product 1

HCID 10824427HCID 10824427, compoundYield 55%

Procedure

A solution of 3-fluoro-4,8-dimethyl-7-allyloxycoumarin (1.56 g, 6.28 mmoles) in 20 mL of N,N-diethylaniline was deoxygenated with argon for 30 minutes and then was heated at reflux for 4 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 methanol:water gave 0.859 g (55% yield) of 3-fluoro-4,8-dimethyl-6-allyl-7-hydroxycoumarin (3, R═F, R′=H) as a white solid: mp 163-164° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 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 methanol

Sources & evidence

ORD record
ord-61a74aa7efd148b1b388affbead806cf
Source dataset
uspto-grants-2001_07
Patent number
US06255324B1

Reaction notes

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