Dimethylformamide → HCID 59496797, compound

HRID 416985Notes

Reaction equation

HRID 416985 reaction equation
[CH2:1]([O:3][C:4](=[O:37])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([OH:28])[CH:25]=[C:24]([Br:29])[CH:23]=2)[C:10]=1[CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH3:2].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.I[CH2:50][CH3:51]>O.CC(C)=O>[CH2:1]([O:3][C:4](=[O:37])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([O:28][CH2:50][CH3:51])[CH:25]=[C:24]([Br:29])[CH:23]=2)[C:10]=1[CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 59496799HCID 59496799, compound

Product 1

HCID 59496797HCID 59496797, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a mixture of 4-[3-[6-(3-bromo-5-hydroxy-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (163 mg, 0.28 mmol) and potassium carbonate (117 mg, 0.84 mmol) were added dimethylformamide (4 mL), acetone (8 mL), and iodoethane (219 mg, 1.4 mmol) at room temperature. The resulting suspension was heated to reflux for 2 days. Then, the reaction mixture was cooled to room temperature and diluted with water (20 mL). The organic compound was extracted into ethyl acetate (2×25 mL) and the combined organic extracts were washed with water (50 mL) and brine solution (50 mL). The organic layers were dried over anhydrous magnesium sulfate and filtration of the drying agent and concentration of the solvent gave the crude product which was purified by using an ISCO 40 g column, eluting with 0-30% ethyl acetate in hexanes to afford 4-[3-[6-(3-bromo-5-ethoxy-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (166 mg, 98%) as a colorless oil: ES(+)-HRMS m/e calcd for C31H43BrO7 (M+H)+ 607.2265. found 607.2270.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux for 2 days
  3. extractionThe organic compound was extracted into ethyl acetate (2×25 mL)
  4. washthe combined organic extracts were washed with water (50 mL) and brine solution (50 mL)
  5. dry with materialThe organic layers were dried over anhydrous magnesium sulfate and filtration of the drying agent and concentration of the solvent
  6. customgave the crude product which
  7. customwas purified
  8. washeluting with 0-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-365f267334e944c0913d7c88363d0e9c
Source dataset
uspto-grants-2012_01
Patent number
US08088936B2

Reaction notes

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