Methanol → HCID 58629750, compound

HRID 423252Notes

Reaction equation

HRID 423252 reaction equation
[H-].[Na+].[CH3:3][OH:4].Br[C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([O:15][CH2:16][CH3:17])[C:13]=1[OH:14])[CH:9]=[O:10]>C1COCC1.CN(C)C=O.C(OCC)(=O)C.[Cu]Cl>[CH2:16]([O:15][C:12]1[CH:11]=[C:8]([CH:7]=[C:6]([O:4][CH3:3])[C:13]=1[OH:14])[CH:9]=[O:10])[CH3:17]

Participants

8

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 6124963-Bromo-5-ethoxy-4-hydroxybenzaldehyde

Product 1

HCID 58629750HCID 58629750, compoundYield 61%

Reagents, catalysts & solvents 4

HCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride (843 mg) in THF (5 mL) was added methanol (675 mg) under ice-cooling, and the mixture was stirred at room temperature for 0.5 hour. 3-Bromo-5-ethoxy-4-hydroxybenzaldehyde (1.29 g) in dimethylformamide (10 mL), and copper(I) chloride (31 mg) were added thereto, and the mixture was stirred at 120° C. for 4 hours under heating. The mixture was allowed to stand for cooling down to room temperature, diluted with ethyl acetate, washed with 1N hydrochloric acid, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1, v/v) to give the title compound (630 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 120° C. for 4 hours
  3. temperatureunder heating
  4. temperaturefor cooling down to room temperature
  5. washwashed with 1N hydrochloric acid
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-49b41d54a7464e5580ec24a5e19d2786
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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