tert-Butanol → 2-(2-chloro-4-fluorobenzyl)-3-oxopentanoic Acid Methyl Ester

HRID 2266577Notes

Reaction equation

HRID 2266577 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].Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[Cl:30]>O1CCCC1.O>[CH3:12][O:13][C:14](=[O:20])[CH:15]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[Cl:30])[C:16](=[O:19])[CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 121699Methyl 3-oxovalerateHCID 27250621-(Bromomethyl)-2-chloro-4-fluorobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 687857022-(2-chloro-4-fluorobenzyl)-3-oxopentanoic Acid Methyl Ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of potassium tert-butoxide (1.6 g) in anhydrous tetrahydrofuran (25 mL) at 0° C. was treated with a mixture of tert-butanol (1.0 mL) and 3-oxopentanoic acid methyl ester (1.5 g). After stirring at 0° C. for 45 minutes a solution of 1-bromomethyl-2-chloro-4-fluorobenzene (2.6 g) in tetrahydrofuran (5.0 mL) was added and the resulting mixture stirred at room temperature for 3 days. The mixture was diluted with water and the tetrahydrofuran removed under reduced pressure. The mixture was extracted with ethyl acetate and the combined extracts dried over magnesium sulfate and the solvent removed under reduced pressure to afford the title compound, 3.2 g.

Workup

  1. additionwas added
  2. customthe tetrahydrofuran removed under reduced pressure
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe combined extracts dried over magnesium sulfate
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-7ba2ea13f1b54cd7b4dc8e20a4ccc40e
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

Loading…