N,N-Diethylaniline → HCID 12900443, compound

HRID 1106267Notes

Reaction equation

HRID 1106267 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([O:12]CC=C)[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:16])[O:7]2.CCOC(C)=O.CCN([C:28]1[CH:29]=CC=C[CH:33]=1)CC>>[CH3:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]([CH2:29][CH:28]=[CH2:33])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:16])[O:7]2

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 8857Ethyl AcetateHCID 129004425-Methyl-7-(2-propen-1-yloxy)-2H-1-benzopyran-2-one

Product 1

HCID 12900443HCID 12900443, compound

Procedure

A solution of 5-methyl-7-allyloxycoumarin (IV; 13.8 g) in diethylaniline (60 ml) was refluxed for 5 hours. After cooling, EtOAc (250 ml) was added and the mixture was washed several times with dil. HCl and then with water; the solvent was evaporated from the dried (Na2SO4) organic phase and the residue by crystallization from EtOAc gave 5-methyl-7-hydroxy-8-allylcoumarin (VIII; 4.5 g; m.p. 177° C.). ##STR11##

Workup

  1. temperatureAfter cooling
  2. washthe mixture was washed several times with dil. HCl
  3. customthe solvent was evaporated from the
  4. dry with materialdried (Na2SO4) organic phase
  5. customthe residue by crystallization from EtOAc

Sources & evidence

ORD record
ord-61452fdb7230476a9d92e22216325476
Source dataset
uspto-grants-1982_01
Patent number
US04312883

Reaction notes

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