Sodium Iodide → HCID 58591566, compound

HRID 746626Notes

Reaction equation

HRID 746626 reaction equation
[Na+].[I-].C[Si](Cl)(C)C.C([O:15][CH2:16][CH2:17][C:18]1[S:22][C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[C:19]=1[C:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1)(O)[CH3:28])C1C=CC=CC=1.C([O-])(O)=O.[Na+]>C(#N)C.CCOC(C)=O>[N:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[CH:27]([C:19]1[C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[S:22][C:18]=1[CH2:17][CH2:16][OH:15])[CH3:28]

Participants

7

Reactant 4

HCID 5238Sodium Iodide2×HCID 6397Chlorotrimethylsilane2×HCID 516892Sodium BicarbonateHCID 69217789HCID 69217789, compound

Product 1

HCID 58591566HCID 58591566, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of NaI (2.29 g, 15.4 mmol) in acetonitrile (45 mL) at room temperature, trimethylsilyl chloride (1.96 mL, 15.4 mmol) was added and the mixture was stirred for 5 min. 1-[2-(2-benzyloxy-ethyl)-benzo[b]thiophen-3-yl]-1-pyridin-2-yl-ethanol (2 g, 5.14 mmol) was added and the mixture was refluxed for 4 hours. An additional aliquot of trimethylsilyl chloride (2.6 mL, 20.5 mmol) and NaI (3.06 g, 20.6 mmol) was added and refluxing was continued for another 6 hours. Sat. NaHCO3 and EtOAc were added and the organic layer was separated. After extraction of the aqueous layers with EtOAc, the combined organic layers were dried (Na2SO4) and concentrated. Silica gel column chromatography (eluent: hexanes up to EtOAc/hexanes=1/1) afforded 2-[3-(1-pyridin-2-yl-ethyl)-benzo[b]thiophen-2-yl]-ethanol in 20% yield.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. temperaturerefluxing
  3. waitwas continued for another 6 hours
  4. customthe organic layer was separated
  5. extractionAfter extraction of the aqueous layers with EtOAc
  6. dry with materialthe combined organic layers were dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c5fbd87aa56245598985d66acbd6bcfb
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

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