tert-Butanol → 2-(2,4-dichlorobenzyl)-3-oxopentanoic Acid Methyl Ester

HRID 2266565Notes

Reaction equation

HRID 2266565 reaction equation
CC(C)([O-])C.[K+].C(O)(C)(C)C.[CH3:12][O:13][C:14](=[O:20])[CH2:15][C:16](=[O:19])[CH2:17][CH3:18].[Cl:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1[CH2:29]Cl>O1CCCC1.O>[CH3:12][O:13][C:14](=[O:20])[CH:15]([CH2:29][C:23]1[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:22]=1[Cl:21])[C:16](=[O:19])[CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 72122,4-Dichlorobenzyl chlorideHCID 121699Methyl 3-oxovalerateHCID 23665647Potassium tert-butoxide

Product 1

HCID 687814912-(2,4-dichlorobenzyl)-3-oxopentanoic Acid Methyl Ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of potassium tert-butoxide (8.4 g) in anhydrous tetrahydrofuran (180 mL) at 0° C. was treated with a mixture of tert-butanol (0.4 mL) and 3-oxopentanoic acid methyl ester (9.8 g). After stirring at room temperature for 30 minutes a solution of 2,4-dichloro-1-chloromethylbenzene (14.7 g) in tetrahydrofuran (20 mL) was added and the resulting mixture warmed to room temperature and then stirred at this temperature for 6 days. The mixture was diluted with water (200 mL), extracted with ethyl acetate and the combined extracts washed with water and saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of pentane and dichloromethane (1:0 to 1:1 by volume) to afford title compound as a white solid, 7.0 g.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washthe combined extracts washed with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue purified by column chromatography on silica gel
  7. washeluting with a mixture of pentane and dichloromethane (1:0 to 1:1 by volume)

Sources & evidence

ORD record
ord-7ba2c4844f9a4e88b3f99dc00193cfaf
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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