tert-Butanol → HCID 66717606, compound

HRID 2266545Notes

Reaction equation

HRID 2266545 reaction equation
CC(C)([O-])C.[K+].C(O)(C)(C)C.[CH2:12]([O:14][C:15](=[O:21])[CH2:16][C:17](=[O:20])[CH2:18][CH3:19])[CH3:13].Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1>O1CCCC1.O>[CH2:12]([O:14][C:15](=[O:21])[CH:16]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:17](=[O:20])[CH2:18][CH3:19])[CH3:13]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 78656Ethyl 3-oxovalerateHCID 23665647Potassium tert-butoxide

Product 1

HCID 66717606HCID 66717606, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of potassium tert-butoxide (7.8 g) in anhydrous tetrahydrofuran (140 mL) at 0° C. was treated with a mixture of tert-butanol (0.3 mL) and 3-oxopentanoic acid ethyl ester (10 g). After stirring at room temperature for 30 minutes a solution of 1-bromomethyl-4-chlorobenzene (14 g) in tetrahydrofuran (20 mL) was added and the resulting mixture stirred at room temperature for 6 days. The mixture was diluted with water, 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 ethyl acetate (1:0 to 10:1 by volume) to afford title compound as a yellow oil, 9.3 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 ethyl acetate (1:0 to 10:1 by volume)

Sources & evidence

ORD record
ord-31b2f344f8714fa4914b321b8bce6e04
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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