Ethyl Acetate → HCID 19079571, compound

HRID 964043Notes

Reaction equation

HRID 964043 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:8]2[CH:9]=[C:10]([OH:13])[CH:11]=[CH:12][C:7]=2[O:6][C:5]=1[C:14]([OH:16])=[O:15].[CH3:17][O:18][CH:19]([O:22][CH3:23])[CH2:20]Br.C(OCC)(=O)C>O1CCOCC1.CN(C)C=O>[CH3:3][C:4]1[C:8]2[CH:9]=[C:10]([O:13][CH2:20][CH:19]([O:22][CH3:23])[O:18][CH3:17])[CH:11]=[CH:12][C:7]=2[O:6][C:5]=1[C:14]([OH:16])=[O:15]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 816722-Bromo-1,1-dimethoxyethaneHCID 14579217HCID 14579217, compound

Product 1

HCID 19079571HCID 19079571, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred slurry of sodium hydride (0.11 g of 60% in oil, 2.7 mmol) in p-dioxane (10 mL) was added methyl 5-hydroxybenzofuran-2-carboxylic acid (0.5 g, 2.6 mmol) and the resulting green slurry was stirred at room temperature for 15 min. To this slurry was added a solution of bromoacetaldehyde dimethyl acetal (0.5 g, 3.0 mmol) in dimethylformamide (DMF) (10 mL) and the resulting solution was heated at reflux for 15 hours. The reaction mixture was poured into ethyl acetate, washed with water, brine, the organic phased dried (Na2SO4) and concentrated in vacuo. The resulting oil was flash chromatographed on silica gel (25% ethyl acetate:hexanes) to afford the title compound as a colorless solid, (0.16 g; m.p. 74-74° C.).

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux for 15 hours
  3. washwashed with water, brine
  4. dry with materialthe organic phased dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel (25% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-a9136515c824452b88ea638ce53bcf8a
Source dataset
uspto-grants-1998_06
Patent number
US05767133

Reaction notes

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