Potassium Iodide → HCID 18421437, compound

HRID 368790Notes

Reaction equation

HRID 368790 reaction equation
[OH:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6]([CH3:26])=[C:7]([CH2:14][N:15]3[C:19](=[O:20])[C:18]4=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]4[C:16]3=[O:25])[C:8](=[O:13])[O:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[Cl:35][C:36]([CH2:38]Cl)=[CH2:37]>CN(C=O)C.C(Cl)Cl>[Cl:35][C:36](=[CH2:37])[CH2:38][O:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6]([CH3:26])=[C:7]([CH2:14][N:15]3[C:16](=[O:25])[C:17]4=[CH:24][CH:23]=[CH:22][CH:21]=[C:18]4[C:19]3=[O:20])[C:8](=[O:13])[O:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 65652,3-DichloropropeneHCID 11430Potassium CarbonateHCID 18421402HCID 18421402, compound

Product 1

HCID 18421437HCID 18421437, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A slurry of 7-hydroxy-4,8-dimethyl-3-phthalimidomethylcoumarin (649 mg, 1.86 mmol), potassium carbonate (320 mg, 2.60 mmol), potassium iodide (15 mg, 0.093 mmol), and 2,3-dichloro-1-propene (0.20 mL, 2.23 mmol) in DMF (15 mL) was stirred at 55-65° C. for 8 hours, allowed to cool to room temperature, then chilled in an ice water bath. The solid was filtered off to obtain the first crop of crude product (1.09 g). Half of the solvent was removed from the filtrate and after chilling, a second crop of crystals was obtained (33 mg). The solids were combined, dissolved in CH2Cl2, and washed with water several times. The organic layer was dried and evaporated to give 7-(beta-chloroallyloxy)-4,8-dimethyl-3-phthalimidomethylcoumarin, a white solid (690 mg, 87%). 1H NMR (CDCl3): δ 7.66-7.83 (m, 4H), 7.49 (d, J=9.1 Hz, 1H), 6.79 (d, J=8.8 Hz, 1H), 5.56 (s, 1H), 5.47 (s, 1H), 4.91 (s, 2H), 4.67 (s, 2H), 2.59 (s, 3H), 2.32 (s, 3H).

Workup

  1. temperaturechilled in an ice water bath
  2. filtrationThe solid was filtered off
  3. customto obtain the first crop of crude product (1.09 g)
  4. customHalf of the solvent was removed from the filtrate
  5. temperatureafter chilling
  6. customa second crop of crystals was obtained (33 mg)
  7. washwashed with water several times
  8. customThe organic layer was dried
  9. customevaporated

Sources & evidence

ORD record
ord-848c89dbf575445f88bda3c72d43cf32
Source dataset
uspto-grants-2000_10
Patent number
US06133460

Reaction notes

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