Methyl iodide → HCID 59678679, compound

HRID 1751848Notes

Reaction equation

HRID 1751848 reaction equation
[OH:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]([N+:14]([O-:16])=[O:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:18])([CH3:17])[O:7]2.[C:19]([O-])([O-])=O.[K+].[K+].CI>>[CH3:19][O:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]([N+:14]([O-:16])=[O:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:18])([CH3:17])[O:7]2

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59678601HCID 59678601, compound

Product 1

HCID 59678679HCID 59678679, compound

Procedure

A mixture of 5-hydroxy-2,2-dimethyl-8-nitro-2H-chromene-6-carbaldehyde (2.34 g, 10 mmol), K2CO3 (4.12 g, 29.8 mmol) and MeI (2.13 g, 0.94 mL, 15 mmol in Me2CO (40 mL) is refluxed for 4 h and stirred at room temperature overnight. The mixture is concentrated, treated with water (15 mL) and extracted with dichloromethane. The combined organic layers are washed with water, dried over Na2SO4, and the solvent is removed in vacuo to afford an oil, which is chromatographed with 3% Me2CO in hexane to afford 5-methoxy-2,2-dimethyl-8-nitro-2H-chromene-6-carbaldehyde.

Workup

  1. temperatureis refluxed for 4 h
  2. concentrationThe mixture is concentrated
  3. additiontreated with water (15 mL)
  4. extractionextracted with dichloromethane
  5. washThe combined organic layers are washed with water
  6. dry with materialdried over Na2SO4
  7. customthe solvent is removed in vacuo
  8. customto afford an oil, which
  9. customis chromatographed with 3% Me2CO in hexane

Sources & evidence

ORD record
ord-588edc8f93ff4dcf82cafeb3364de506
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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