tert-Butanol → 2-[4-(morpholine-4-sulfonyl)benzyl]-3-oxopentanoic Acid Methyl Ester

HRID 2266598Notes

Reaction equation

HRID 2266598 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]([S:29]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)(=[O:31])=[O:30])=[CH:25][CH:24]=1>O1CCCC1>[CH3:12][O:13][C:14](=[O:20])[CH:15]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)(=[O:31])=[O:30])=[CH:25][CH:24]=1)[C:16](=[O:19])[CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 121699Methyl 3-oxovalerateHCID 27796804-((4-(Bromomethyl)phenyl)sulfonyl)morpholineHCID 23665647Potassium tert-butoxide

Product 1

HCID 687842512-[4-(morpholine-4-sulfonyl)benzyl]-3-oxopentanoic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of potassium tert-butoxide (0.26 g) in anhydrous tetrahydrofuran (40 mL) at 0° C. was treated with a mixture of tert-butanol (1.0 mL) and 3-oxopentanoic acid methyl ester (0.25 mL). The mixture was stirred at 0° C. for 45 minutes and then a solution of 4-(4-bromomethylbenzenesulfonyl)morpholine (0.53 g) in tetrahydrofuran (10 mL) was added and the resulting mixture warmed to room temperature over 1 hour and then stirred at this temperature for 17 hours. The mixture was concentrated under reduced pressure and the residue diluted with water and 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 ethyl acetate and cyclohexane (1:1 by volume) to afford title compound, 0.41 g.

Workup

  1. temperaturethe resulting mixture warmed to room temperature over 1 hour
  2. stirringstirred at this temperature for 17 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionthe residue diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe combined extracts were washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe residue purified by column chromatography on silica gel
  10. washeluting with a mixture of ethyl acetate and cyclohexane (1:1 by volume)

Sources & evidence

ORD record
ord-3eae3e8443ad4797b7246d6098f91502
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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