Methyl iodide → HCID 21981050, compound

HRID 10658Notes

Reaction equation

HRID 10658 reaction equation
[S:1]1[C:5]([C:6]2[C:7]([OH:16])=[C:8]([CH:11]=[CH:12][C:13]=2[O:14][CH3:15])[CH:9]=[O:10])=[CH:4][C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]1=2.[C:21](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[S:1]1[C:5]([C:6]2[C:7]([O:16][CH3:21])=[C:8]([CH:11]=[CH:12][C:13]=2[O:14][CH3:15])[CH:9]=[O:10])=[CH:4][C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]1=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 219811163-Benzo[b]thiophen-2-yl-2-hydroxy-4-methoxy-benzaldehyde

Product 1

HCID 21981050HCID 21981050, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ex-44B: 3-Benzo[b]thiophen-2-yl-2-hydroxy-4-methoxy-benzaldehyde (Ex-44A, 57.4 mg, 0.202 mmol) was dissolved in acetone (5 mL) and potassium carbonate (31 mg, 0.22 mmol) was added. Methyl iodide (25 uL, 0.40 mmol) was added and the solution was heated to reflux for 3.5 h. After cooling, the crude reaction mix was concentrated on the rotavap. The resulting residue was taken up in 10 mL of a 1:9 mix of saturated, aqueous NH4Cl to water and extracted with EtOAc (2×15 mL). The organic phase was dried over sodium sulfate, filtered, and concentrated to provide 58.5 mg of 3-benzo[b]thiophen-2-yl-2,4-dimethoxy-benzaldehyde as an orange, oily residue which was used without further purification, 97% yield. 1H-NMR (CDCl3) δ 10.31 (s, 1H), 7.92 (d, J=9 Hz, 1H), 7.81–7.88 (m, 2H), 7.56 (d, 1H), 7.33–7.39 (m, 2H), 6.88 (d, J=9 Hz, 1H), 3.91 (s, 3H), 3.64 (s, 3H).

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 3.5 h
  3. temperatureAfter cooling
  4. customthe crude reaction
  5. additionmix
  6. concentrationwas concentrated on the rotavap
  7. additionmix of saturated, aqueous NH4Cl to water
  8. extractionextracted with EtOAc (2×15 mL)
  9. dry with materialThe organic phase was dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-7070a2403dc04cfaa55f901c61e6fa83
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

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