tert-Butanol → HCID 68782740, compound

HRID 2266562Notes

Reaction equation

HRID 2266562 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[F: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[F:30])[C:16](=[O:19])[CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 121699Methyl 3-oxovalerateHCID 23665647Potassium tert-butoxide

Product 1

HCID 68782740HCID 68782740, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of potassium tert-butoxide (3.2 g) in anhydrous tetrahydrofuran (40 mL) at 0° C. was treated with a mixture of tert-butanol (0.15 mL) and 3-oxopentanoic acid methyl ester (3.8 g). The mixture was warmed to room temperature over 30 minutes and then a solution of 1-bromomethyl-2,4-difluorobenzene (6.0 g) in tetrahydrofuran (10 mL) was added and the resulting mixture stirred at room temperature for 72 hours. The mixture was diluted with water (10 mL) and the tetrahydrofuran removed under reduced pressure. The residue was partitioned between ethyl acetate and dilute aqueous ammonium chloride solution and the aqueous phase extracted with diethyl ether. The combined organic phases were dried over magnesium sulfate and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of toluene, dichloromethane and ethyl acetate (4:1:0 to 0:1:0 to 0:25:1 by volume) to afford title compound as colourless oil, 4.5 g.

Workup

  1. customthe tetrahydrofuran removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and dilute aqueous ammonium chloride solution
  3. extractionthe aqueous phase extracted with diethyl ether
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. customthe solvent removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with a mixture of toluene, dichloromethane and ethyl acetate (4:1:0 to 0:1:0 to 0:25:1 by volume)

Sources & evidence

ORD record
ord-8fc1598719a64b85a27fc8dfce1ec197
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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