Ethyl Acetate → HCID 66750567, compound

HRID 643879Notes

Reaction equation

HRID 643879 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]([OH:15])=[CH:13][C:12]2[C:7](=[CH:8][C:9]([OH:16])=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].[C:17]([O:21][C:22](=[O:25])[CH2:23]Br)([CH3:20])([CH3:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:14]([OH:15])=[CH:13][C:12]2[C:7](=[CH:8][C:9]([O:16][CH2:23][C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:25])=[CH:10][CH:11]=2)[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 22173744HCID 22173744, compound

Product 1

HCID 66750567HCID 66750567, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3,7-dihydroxynaphthalene-2-carboxylic acid methyl ester (3.32 g, 15.5 mmol), bromoacetic acid tert-butyl ester (2.29 mL, 15.5 mmol) and potassium carbonate (4.28 g, 31.0 mmol) in DMF (20 mL) is stirred at 60° C. for 18 h. The reaction mixture is poured to EtOAc, wash with water and brine. It is then dried with MgSO4 and concentrated to give the title compound.

Workup

  1. washwash with water and brine
  2. dry with materialIt is then dried with MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2d2f939adb0d4254b87d1e09a8b2ceb0
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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