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Sodium Iodide → 7-((2-Methoxy-4-propylbenzyl)oxy)-2H-chromene-3-carbaldehyde

HRID 217443
Notes
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Reaction equation

HRID 217443 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH3:11])=[CH:5][C:4]=1[O:12][CH3:13].[OH:14][C:15]1[CH:24]=[C:23]2[C:18]([CH:19]=[C:20]([CH:25]=[O:26])[CH2:21][O:22]2)=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].[I-].[Na+]>CN(C=O)C.O>[CH3:13][O:12][C:4]1[CH:5]=[C:6]([CH2:9][CH2:10][CH3:11])[CH:7]=[CH:8][C:3]=1[CH2:2][O:14][C:15]1[CH:24]=[C:23]2[C:18]([CH:19]=[C:20]([CH:25]=[O:26])[CH2:21][O:22]2)=[CH:17][CH:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 167691667-Hydroxy-2H-chromene-3-carbaldehydeHCID 666944811-(Chloromethyl)-2-methoxy-4-propylbenzene

Product 1

HCID 584387817-((2-Methoxy-4-propylbenzyl)oxy)-2H-chromene-3-carbaldehydeYield 64.6%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1-(chloromethyl)-2-methoxy-4-propylbenzene (1.1 g) was dissolved in DMF (20 mL), and 7-hydroxy-2H-chromene-3-carbaldehyde (975 mg) and K2CO3 (1.15 g) were added thereto, followed by stirring at 80° C. for 1 hour. Further, sodium iodide (416 mg) was added thereto, followed by stirring at 80° C. for 1 hour. After confirming completion of the reaction, to the reaction liquid was added water to stop the reaction, followed by extraction with EtOAc three times. The organic layer was combined, washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=95:5 to 80:20) to obtain 7-[(2-methoxy-4-propylbenzyl)oxy]-2H-chromene-3-carbaldehyde (1.21 g) as a yellow powder.

Workup

  1. stirringby stirring at 80° C. for 1 hour
  2. customcompletion of the reaction
  3. customto the reaction liquid
  4. customthe reaction
  5. extractionfollowed by extraction with EtOAc three times
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=95:5 to 80:20)

Sources & evidence

ORD record
ord-e78c67ab66284f02871a8ca1fa7d3a9e
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08193378B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes