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

HRID 217443Notes

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

Participants

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

stirringby stirring at 80° C. for 1 hour
customcompletion of the reaction
customto the reaction liquid
customthe reaction
extractionfollowed by extraction with EtOAc three times
washwashed with brine
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
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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