Water → HCID 9884329, compound

HRID 1603640Notes

Reaction equation

HRID 1603640 reaction equation
O.[CH2:2]([S:9][CH:10]1[NH:13][C:12](=[O:14])[CH2:11]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:16][C:17](=[O:26])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[CH2:2]([S:9][CH:10]1[N:13]([CH2:16][C:17](=[O:26])[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:12](=[O:14])[CH2:11]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14797Potassium HydroxideHCID 126080271-Bromo-4-phenylbutan-2-oneHCID 19605253HCID 19605253, compound

Product 1

HCID 9884329HCID 9884329, compoundYield 32.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (cold water bath) solution of 4-(benzylthio)azetidin-2-one (5.5 g, 28.5 mmol), tetra-n-butylammonium bromide (0.9 g, 2.85 mmol) and 1-bromo-4-phenylbutan-2-one (7.1 g, 31.3 mmol) in dry THF (100 ml) was added freshly powdered potassium hydroxide (1.8 g, 31.3 mmol), and the mixture stirred vigorously for 2 hr at ambient temperature. Water was added and the product extracted into ethyl acetate, dried (MgSO4) and evaporated to an oil. Treatment with ether gave the product as a white crystalline solid (3.12 g, 32%) mp 79-81° C.

Workup

  1. extractionthe product extracted into ethyl acetate
  2. dry with materialdried (MgSO4)
  3. customevaporated to an oil

Sources & evidence

ORD record
ord-eb49bd26afa942d6a42ec00862c49f68
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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