Dimethylformamide → HCID 68956549, compound

HRID 1045029Notes

Reaction equation

HRID 1045029 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.Br[CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[O:1][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 7016416BENZYL 3-HYDROXYPHENYLACETATE

Product 1

HCID 68956549HCID 68956549, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of benzyl 2-(3-hydroxyphenyl)acetate (1.39 g, 5.74 mmol), ethyl 4-bromobutanoate (1.23 g, 6.3 mmol), anhydrous K2CO3 (1.98 g, 14.4 mmol) and anhydrous DMF (10 mL) was stirred at room temperature overnight. Water was added to the mixture and extracted with ethyl acetate. The organic layer was washed with water, brine, dried (Na2SO4) and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate in petroleum ether, 25% to 50% v/v) to yield ethyl 4-(3-(2-(benzyloxy)-2-oxoethyl)phenoxy)butanoate (2.05 g, 100%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 1.17 (t, J=7.2 Hz, 3H), 1.96 (m, 2H), 2.45 (t, J=7.2 Hz, 2H), δ 3.70 (s, 2H), 3.94 (t, J=6.4 Hz, 2H), 4.07 (q, J=7.2 Hz, 2H), 5.11 (s, 2H), 6.83 (m, 3H), 7.20 (t, 1H), 7.20 (m, 5H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate in petroleum ether, 25% to 50% v/v)

Sources & evidence

ORD record
ord-dc73400dfcbc437f8f31ee87ca66b662
Source dataset
uspto-grants-2013_10
Patent number
US08563741B2

Reaction notes

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