Sodium hydride → Tert-butyl 3-(2-methyl-2-oxiranyl)propionate

HRID 856135Notes

Reaction equation

HRID 856135 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[O:9]=[C:10]([CH3:20])[CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>CS(C)=O>[CH3:20][C:10]1([CH2:11][CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:2][O:9]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 15577827tert-Butyl 4-oxopentanoate

Product 1

HCID 23081086Tert-butyl 3-(2-methyl-2-oxiranyl)propionateYield 67.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Trimethylsulfoxonium iodide (19.54 g, 88.78 mmol) was added to a suspension of sodium hydride (3.71 g, 92.82 mmol) in DMSO (50 ml) while cooling in an ice-bath, and the mixture was stirred for 2.5 hours. To which a solution of tert-butyl 4-oxopentanoate (13.90 g, 80.71 mmol) in DMSO (20 ml) was added, and the mixture was stirred at room temperature for 15 hours. The mixture was poured into ice water, extracted with diethyl ether. The extract was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure to afford tert-butyl 3-(2-methyl-2-oxiranyl)propionate (10.1 g, yield 67%) as a pale yellow oil.

Workup

  1. temperaturewhile cooling in an ice-bath
  2. stirringthe mixture was stirred at room temperature for 15 hours
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-03118e18fe5746af891be8b7416428bb
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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