Acetone → HCID 21866714, compound

HRID 890674Notes

Reaction equation

HRID 890674 reaction equation
[OH-:1].[Na+].[C:3]([S:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[N:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[O:16][C:17]=1[CH3:18])(=O)[CH3:4].ClC(Cl)(Cl)[C:28](C)([OH:30])C.[H-].[CH3:35]C(C)=O>O>[CH3:4][C:3]([S:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[N:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[O:16][C:17]=1[CH3:18])([CH3:35])[C:28]([OH:30])=[O:1]

Participants

7

Reactant 5

HCID 180AcetoneHCID 5977ChlorobutanolHCID 14798Sodium Hydroxide2×HCID 166653HydrideHCID 21866825HCID 21866825, compound

Product 1

HCID 21866714HCID 21866714, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under argon atmosphere, 24 mg of triturated sodium hydroxide was added to 2 ml of a solution of 100 mg of 4-(6-acetylthiohexyl)-5-methyl-2-(p-tolyl)oxazole in acetone, and stirred for 2 hours at room temperature. To the reaction solution, 20 μl of water was added, followed by addition of 113 mg of 1,1,1-trichloro-2-methyl-2-propanol.0.5 hydride (chloretone), and then 96.5 mg of triturated sodium hydroxide in tree portions at 30 minutes intervals. The mixture was stirred for additional 18 hours at room temperature. The reaction solution was concentrated. The residue was, after addition of water, extracted with diethyl ether. The organic layers were combined, washed with water, and the washings was acidified with 1 N hydrochloric acid and extracted with ethyl acetate. The organic layers were combined, washed with water and brine sequentially, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (Wakogel® C-200, chloroform:methanol=100:1) and the resulting crystals were washed with n-hexane to provide 28.0 mg of the objective compound as pale yellow crystals.

Workup

  1. stirringThe mixture was stirred for additional 18 hours at room temperature
  2. concentrationThe reaction solution was concentrated
  3. additionafter addition of water
  4. extractionextracted with diethyl ether
  5. washwashed with water
  6. extractionextracted with ethyl acetate
  7. washwashed with water and brine sequentially
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, chloroform:methanol=100:1)
  11. washthe resulting crystals were washed with n-hexane

Sources & evidence

ORD record
ord-d312d4b397b14cadb2064823b39b5e7e
Source dataset
uspto-grants-2006_02
Patent number
US06998412B2

Reaction notes

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