tert-Butanol → HCID 68783429, compound

HRID 2266535Notes

Reaction equation

HRID 2266535 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].Cl[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1>O1CCCC1.O>[CH3:12][O:13][C:14](=[O:20])[CH:15]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:28]=1)[C:16](=[O:19])[CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 121699Methyl 3-oxovalerateHCID 1235301-(Chloromethyl)-4-methanesulfonylbenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 68783429HCID 68783429, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

A suspension of potassium tert-butoxide (2.7 g) in anhydrous tetrahydrofuran (35 mL) at 0° C. was treated with a mixture of tert-butanol (0.1 mL) and 3-oxopentanoic acid methyl ester (3.2 g). After stirring at room temperature for 15 minutes a solution of 1-chloromethyl-4-methanesulfonylbenzene (5.0 g) in tetrahydrofuran (15 mL) was added and the resulting mixture heated at 70° C. for 16 hours. The mixture was cooled to room temperature, diluted with water and the tetrahydrofuran removed under reduced pressure. The residue was partitioned between ethyl acetate and dilute aqueous ammonium chloride solution. The aqueous phase was extracted with ethyl acetate and the combined organic phases 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 toluene, dichloromethane and ethyl acetate (1:1:0 to 0:1:0 to 0:4:1 by volume) to afford title compound as a waxy white solid, 3.0 g.

Workup

  1. additionwas added
  2. temperatureThe mixture was cooled to room temperature
  3. customthe tetrahydrofuran removed under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and dilute aqueous ammonium chloride solution
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. dry with materialthe combined organic phases dried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue purified by column chromatography on silica gel
  9. washeluting with a mixture of toluene, dichloromethane and ethyl acetate (1:1:0 to 0:1:0 to 0:4:1 by volume)

Sources & evidence

ORD record
ord-957066c227064e3aad88ef069f32f38b
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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