Potassium Iodide → HCID 22012178, compound

HRID 1377504Notes

Reaction equation

HRID 1377504 reaction equation
[S:1]1[CH2:5][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]1=2.Br[CH2:12][CH2:13][C:14](OCC)=[O:15].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].C(OC(C)C)(C)C>CC(C)=O>[S:1]1[CH:5]=[C:4]([O:6][CH2:12][CH2:13][CH2:14][OH:15])[C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]1=2

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 7914Diisopropyl EtherHCID 11430Potassium CarbonateHCID 68320Ethyl 3-bromopropionateHCID 109864131-BENZOTHIOPHEN-3(2H)-ONE

Product 1

HCID 22012178HCID 22012178, compoundYield 1.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of benzo[b]thiophen-3-one (30 g), ethyl 3-bromopropionate (73 g), potassium carbonate (55 g), potassium iodide (1.3 g) and acetone (600 ml) was refluxed for 18 h. Filtration and removal of solvent in vacuo a red oil which was dissolved in ether (200 ml) and dried over magnesium sulfate. The ether solution was added dropwise to a suspension of lithium aluminium hydride (5 g) in ether (100ml) followed by reflux for 1 h. Usual work-up gave a viscous oil which was applied to a silica gel Column (eluent:isopropyl ether) giving 3-(benzo[b]thiophen-3-yloxy)-1-propanol (0.54 g) as an oil. The title compound was obtained according to the method described in EXAMPLE 2 using spiro[isobenzofuran-1(3H),4'-piperidine] and crystallized as the maleate salt from an acetone/ether mixture by addition of maleic acid. Yield: 0.34 g, mp: 116°-17° C.

Workup

  1. temperaturewas refluxed for 18 h
  2. filtrationFiltration and removal of solvent in vacuo a red oil which
  3. dissolutionwas dissolved in ether (200 ml)
  4. dry with materialdried over magnesium sulfate
  5. additionThe ether solution was added dropwise to a suspension of lithium aluminium hydride (5 g) in ether (100ml)
  6. temperatureby reflux for 1 h
  7. customUsual work-up gave a viscous oil which

Sources & evidence

ORD record
ord-ba7fa1523ac94b3594361a66d32209ac
Source dataset
uspto-grants-1997_09
Patent number
US05665725

Reaction notes

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