Ethyl bromoacetate → HCID 11425546, compound

HRID 843122Notes

Reaction equation

HRID 843122 reaction equation
[CH:1]1([C:4]([C:6]2[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:7]=2[OH:13])=[O:5])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:20]([O:22][C:23](=[O:26])[CH2:24]Br)[CH3:21]>CC(C)=O.C(OCC)(=O)C>[CH2:20]([O:22][C:23](=[O:26])[CH2:24][O:13][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([OH:12])[C:6]=1[C:4]([CH:1]1[CH2:2][CH2:3]1)=[O:5])[CH3:21]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 11148052HCID 11148052, compound

Product 1

HCID 11425546HCID 11425546, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of cyclopropyl-(2,6-dihydroxy-phenyl)-methanone (398 mg) and potassium carbonate (500 mg) in acetone (5 ml) was added bromoacetic acid ethyl ester (300 μl) at room temperature. The suspension was heated to reflux for 1.5 hours and diluted with ethyl acetate (10 ml), washed with diluted hydrochloric acid (5 ml) and brine (5 ml), dried over anhydrous sodium sulfate, then concentrated in vacuo. The mixture was purified by silica gel column chromatography developed by hexane-ethyl acetate to give (2-cyclopropanecarbonyl-3-hydroxy-phenoxy)-acetic acid ethyl ester as a pale yellow solid (382 mg). EI-MS: m/z 264 (M+); 1H-NMR (CDCl3): δ 1.04-1.09 (2H, m), 1.23-1.29 (2H, m), 1.28 (3H, t, J=7.26 Hz), 2.26-2.35 (1H, m), 4.29 (2H, q, J=7.26 Hz), 4.70 (2H, s), 6.27 (1H, dd J=0.99 Hz, 8.25 Hz), 6.62 (1H, dd, J=0.99 Hz, 8.25 Hz), 6.41 (2H, d, J=8.25 Hz), 7.31 (1H, dd, J=8.25 Hz, 8.25 Hz), 12.89 (1H, s).

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 1.5 hours
  3. washwashed with diluted hydrochloric acid (5 ml) and brine (5 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cb0069aff4434ecdaf3dfc94d51d1c78
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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