Lithium hydride → HCID 59496799, compound

HRID 416984Notes

Reaction equation

HRID 416984 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[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]Br)[C:10]=1[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:2].[Br:30][C:31]1[CH:32]=[C:33]([OH:38])[CH:34]=[C:35]([OH:37])[CH:36]=1.[H-].[Li+]>CS(C)=O.O>[CH2:1]([O:3][C:4](=[O:29])[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:37][C:35]2[CH:34]=[C:33]([OH:38])[CH:32]=[C:31]([Br:30])[CH:36]=2)[C:10]=1[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:2]

Participants

6

Reactant 3

HCID 62714Lithium hydrideHCID 5573835-bromobenzene-1,3-diolHCID 575864914-[3-(6-Bromo-hexyl)-2-(ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

Product 1

HCID 59496799HCID 59496799, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 4-[3-(6-bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (4.48 g, 9.5 mmol) and 5-bromo-benzene-1,3-diol (1.79 g, 9.47 mmol) in dimethylsulfoxide (30 mL) was added lithium hydride (160 mg, 20 mmol) at room temperature. The resulting suspension was stirred for 48 h and then the reaction mixture was diluted with water (100 mL). The organic compound was extracted into ethyl acetate (3×50 mL) and the combined organic extracts were washed with water (100 mL) and brine solution (100 mL). The organic layers were dried over anhydrous magnesium sulfate and filtration of the drying agent and concentration of the solvent under vacuum gave the crude product which was purified by using an ISCO 120 g column, eluting with 0-30% ethyl acetate in hexanes to afford 4-[3-[6-(3-bromo-5-hydroxy-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (2.73 g, 74%) as a white solid: ES(+)-HRMS m/e calcd for C29H39BrO7 (M+Na)+ 601.1771, found 601.1773.

Workup

  1. extractionThe organic compound was extracted into ethyl acetate (3×50 mL)
  2. washthe combined organic extracts were washed with water (100 mL) and brine solution (100 mL)
  3. dry with materialThe organic layers were dried over anhydrous magnesium sulfate and filtration of the drying agent and concentration of the solvent under vacuum
  4. customgave the crude product which
  5. customwas purified
  6. washeluting with 0-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c9717640fc3046d8982624cd75bd0651
Source dataset
uspto-grants-2012_01
Patent number
US08088936B2

Reaction notes

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