Sodium hydride → 4-Methylthio-1-(4-phenyl-2-oxobutyl)azetidin-2-one

HRID 1420524Notes

Reaction equation

HRID 1420524 reaction equation
[CH3:1][S:2][CH:3]1[NH:6][C:5](=[O:7])[CH2:4]1.[H-].[Na+].Br[CH2:11][C:12](=[O:21])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH3:1][S:2][CH:3]1[N:6]([CH2:11][C:12](=[O:21])[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5](=[O:7])[CH2:4]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 126080271-Bromo-4-phenylbutan-2-oneHCID 126772484-(Methylsulfanyl)azetidin-2-one

Product 1

HCID 187820304-Methylthio-1-(4-phenyl-2-oxobutyl)azetidin-2-oneYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 4-methylthioazetidin-2-one (Clauss K, Grimm D, Prossel G, Anal, 1974, 539) (1.17 g, 0.01 mol) in THF (lOml) was added dropwise over 5 minutes to a suspension of sodium hydride (0.42 g, 0.01 mol) in dry THF (30 ml) under a nitrogen atmosphere at -10° C. The mixture was stirred for 15 minutes whilst keeping the temperature between -5 and -10° C. 1-Bromo-4-phenylbutan-2-one (Tetrahedron, 1970, 26, 5611) (2.27 g, 0.01 mol) in dry THF (10 ml) was added over 5 minutes at -10° C. The resultant mixture was stirred at room temperature for 1 hour then poured onto ice/water (100 g), filtered through Hyflo, washed with brine and separated. The organic extract was dried and evaporated under reduced pressure to a yellow oil. This was purified by flash chromatography on silica gel using petroleum ether/ethyl acetate 2:1, to give 4-methylthio-1-(4-phenyl-2-oxobutyl)azetidin-2-one as a colourless oil (1.08 g, 41%).

Workup

  1. customthe temperature between -5 and -10° C
  2. additionthen poured onto ice/water (100 g)
  3. filtrationfiltered through Hyflo
  4. washwashed with brine
  5. customseparated
  6. extractionThe organic extract
  7. customwas dried
  8. customevaporated under reduced pressure to a yellow oil
  9. customThis was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-72aa70abd87e4c45b9c185faf4a0ad62
Source dataset
uspto-grants-2000_06
Patent number
US06071899

Reaction notes

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