Water → HCID 14684538, compound

HRID 1719709Notes

Reaction equation

HRID 1719709 reaction equation
[CH2:1]([Li])CCC.[I-].C[S+](C)C.[C:11]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)(=[O:14])[CH2:12][CH3:13].O>CCCCCC.C1COCC1>[CH2:12]([C:11]1([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH2:1][O:14]1)[CH3:13]

Participants

7

Reactant 4

HCID 962WaterHCID 743431-(4-Pyridinyl)-1-propanoneHCID 75127Trimethylsulfonium iodideHCID 178418339Butyllithium

Product 1

HCID 14684538HCID 14684538, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

n-Butyl lithium (7.3 cm3 of a 1.6M solution in hexane) was added at 0° to a stirred suspension of trimethyl sulphonium iodide (2.45 g) in THF (40 cm3) under nitrogen. After 5 minutes 4-propionylpyridine (1.35 g) in THF (5 cm3) was added, the mixture was allowed to warm to room temperature over 1.5 hours, water (20 cm3) was added and volatile material was removed in vacuo. The residue was partitioned between ether and water, the ethereal layer was dried (MgSO4) and evaporated and the residue was chromatographed on silica ("Merck" 60.9385) eluting with methanol:chloroform, 1:49, to give 2-ethyl-2-(4-pyridyl)oxirane as an oil (0.6 g). This material was taken without further purification into DMF (5 cm3) and treated with a solution of 2-sodioisothiazolidine-1,1-dioxide [made from isothiazolidine-1,1-dioxide (0.6 g) and sodium hydride (0.30 g of a 50% dispersion in oil)] in DMF (2 cm3) at 100° for 4 hours. Volatile material was removed in vacuo, the residue was partitioned between ethyl acetate (20 cm3) and water (10 cm3) and the aqueous phase was further extracted with ethyl acetate (2×20 cm3). The combined extracts were dried (MgSO4) and evaporated, and the residue was chromatographed on silica ("Merck" 60.9385) eluting with methanol:chloroform, 1:49, to afford 2-[2-(4-pyridyl)-2-hydroxy]but-1-ylisothiazolidine-1,1-dioxide as an oil.

Workup

  1. customvolatile material was removed in vacuo
  2. customThe residue was partitioned between ether and water
  3. dry with materialthe ethereal layer was dried (MgSO4)
  4. customevaporated
  5. customthe residue was chromatographed on silica ("Merck" 60.9385)
  6. washeluting with methanol

Sources & evidence

ORD record
ord-2015f547174f40c698a983d83563d981
Source dataset
uspto-grants-1985_09
Patent number
US04542132

Reaction notes

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