Chloroform → 4-Benzyloxy-7-(2-[4-fluorophenyl]ethoxy)coumarin

HRID 2163713Notes

Reaction equation

HRID 2163713 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=2)[O:12][C:11](=[O:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1.C(Cl)(Cl)Cl>CC(C)=O>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)=[CH:16][CH:17]=2)[O:12][C:11](=[O:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 5731534-Fluorophenethyl bromideHCID 134084074-Benzyloxy-7-hydroxycoumarin

Product 1

HCID 227513064-Benzyloxy-7-(2-[4-fluorophenyl]ethoxy)coumarin

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-benzyloxy-7-hydroxycoumarin (5.36; 0.02 mole) anhydrous potassium carbonate (4.0g) and 1-bromo-2-(4-fluorophenyl) ethane (4.06g) in acetone (100ml) was stirred at reflux for 20 hours and the inorganic material filtered off. Evaporation of the filtrate in vacuo gave an oil which rapidly set solid on scratching. Chloroform (200ml) was added and the mixture filtered to remove unchanged 4-benzyloxy-7-hydroxycoumarin. Reevaporation of the filtrate afforded a white solid, 3.34g (43%) of m.p. 120°,νmax (mull) 1715, 1675, 1620cm-1 ; τ(CDCl3); 6.93 (2H, t, J 6.7Hz); 5.80 (2H, t, J 6.7Hz); 4.87 (2H,S); 4.38 (1H,); 3.29-2.49 (6H, m) 2.32 (1H, d, J 10Hz); (Found C, 73.75 H,5.14 C24H19FO4 requires; C, 73.84; H, 4.91%).

Workup

  1. temperatureat reflux for 20 hours
  2. filtrationthe inorganic material filtered off
  3. customEvaporation of the filtrate in vacuo
  4. customgave an oil which rapidly set solid
  5. filtrationthe mixture filtered
  6. customto remove unchanged 4-benzyloxy-7-hydroxycoumarin
  7. customReevaporation of the filtrate
  8. customafforded a white solid, 3.34g (43%) of m.p. 120°,νmax (mull) 1715, 1675, 1620cm-1

Sources & evidence

ORD record
ord-9f9facb95fe340dbb588efe901358512
Source dataset
uspto-grants-1979_01
Patent number
US04136192

Reaction notes

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