Sodium Bicarbonate → HCID 68834690, compound

HRID 1623029Notes

Reaction equation

HRID 1623029 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][CH2:6][OH:7].[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1B(O)O.C([O-])(O)=O.[Na+]>COCCOC>[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH:5]([C:4]1[CH:8]=[CH:9][CH:10]=[CH:2][CH:3]=1)[CH2:6][OH:7]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27339602-Thiopheneboronic acidHCID 27340902-(3-Bromophenyl)ethan-1-ol

Product 1

HCID 68834690HCID 68834690, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

3-Bromophenethyl alcohol (4 ml, 29.8 mmol) was dissolved in 1,2-dimethoxyethane (225 mL) and mixed with tetrakistriphenylphosphine palladium[0] (2.6 g, 2.25 mmol) at room temperature. The reaction mixture was then added to a solution of 2-thienyl-boronic acid (12.6 g, 99 mmol) and 1N NaHCO3 (90 mL). The reaction mixture was heated to reflux under nitrogen atmosphere for 48 hours. The reaction mixture was partitioned with water and ethyl acetate. The organic layer was dried with MgSO4, filtered through a plug of silica and the solvent was evaporated in vacuo to yield a crude oil. The crude oil was purified via flash chromatography (30% EtOAc/hexane) to yield the title compounds as an oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under nitrogen atmosphere for 48 hours
  3. customThe reaction mixture was partitioned with water and ethyl acetate
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered through a plug of silica
  6. customthe solvent was evaporated in vacuo
  7. customto yield a crude oil
  8. customThe crude oil was purified via flash chromatography (30% EtOAc/hexane)

Sources & evidence

ORD record
ord-57975649e3874abeb5eab0c3f4c18f12
Source dataset
uspto-grants-2014_07
Patent number
US08778956B2

Reaction notes

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