tert-Butanol → HCID 68783725, compound

HRID 2266485Notes

Reaction equation

HRID 2266485 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]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1>O1CCCC1.O>[CH2:12]([O:14][C:15](=[O:21])[CH:16]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][CH:29]=1)[C:17](=[O:20])[CH2:18][CH3:19])[CH3:13]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 78656Ethyl 3-oxovalerateHCID 27335814-(Methylsulfonyl)benzyl BromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 68783725HCID 68783725, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

A suspension of potassium tert-butoxide (3.9 g) in anhydrous tetrahydrofuran (60 mL) at 0° C. was treated with a mixture of tert-butanol (0.15 mL) and 3-oxopentanoic acid ethyl ester (5.0 g). The mixture was warmed to room temperature and after 30 minutes a solution of 1-bromomethyl-4-methanesulfonylbenzene (8.6 g) in tetrahydrofuran (20 mL) was added and the resulting mixture heated at 70° C. for 17 hours. The mixture was cooled to room temperature and diluted with water (20 mL) and this mixture was extracted with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride solution and 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 dichloromethane and ethyl acetate (1:0 to 4:1 by volume) to afford title compound as a white solid, 3.6 g.

Workup

  1. additionwas added
  2. temperatureThe mixture was cooled to room temperature
  3. extractionthis mixture was extracted with ethyl acetate
  4. washThe combined extracts were washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue purified, by column chromatography on silica gel
  8. washeluting with a mixture of dichloromethane and ethyl acetate (1:0 to 4:1 by volume)

Sources & evidence

ORD record
ord-5c56e09a1d8345d4a1cc020ecd3ff708
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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