Dimethylformamide → HCID 22223280, compound

HRID 1744768Notes

Reaction equation

HRID 1744768 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9](O)=[C:8]2[C:3]=1[CH2:4][CH:5]=[C:6]([CH3:13])[CH2:7]2.[H-].[Na+].[CH3:16]I.CN([CH:21]=[O:22])C>C(OCC)(=O)C>[CH3:16][O:1][C:2]1[CH:11]=[CH:10][C:9]([O:22][CH3:21])=[C:8]2[C:3]=1[CH2:4][CH:5]=[C:6]([CH3:13])[CH2:7]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10535268HCID 10535268, compound

Product 1

HCID 22223280HCID 22223280, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a cold (−78° C.) solution of hydroquinone 3 (17.00 g, 96.6 mmol) in DMF under N2 was added unwashed 60% sodium hydride in mineral oil (8.90 g, 222.5 mmol). The resultant reaction mixture was warmed to room temperature over a 30 min period and subsequently treated with methyl iodide (14.3 mL, 230 mmol). After stirring the reaction mixture for 1 hr at room temperature the reaction mixture was diluted with ethyl acetate (1.5 L) and washed with brine (3×500 ml). The organic solution was dried over sodium sulfate, filtered, concentrated, and the residue purified on silica gel (elution with 20% ethyl acetatehexane) to afford 4 as a light yellow oil which solidified upon standing.

Workup

  1. customThe resultant reaction mixture
  2. washwashed with brine (3×500 ml)
  3. dry with materialThe organic solution was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue purified on silica gel (elution with 20% ethyl acetatehexane)

Sources & evidence

ORD record
ord-0a4c1fb3fe8d48b8b51796bff02b45f8
Source dataset
uspto-grants-2006_03
Patent number
US07018797B2

Reaction notes

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