Sodium Bicarbonate → HCID 22136231, compound

HRID 1827295Notes

Reaction equation

HRID 1827295 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][CH2:11][OH:12].[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O.C([O-])(O)=O.[Na+]>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][CH2:11][OH:12]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 27339602-Thiopheneboronic acidHCID 22136233HCID 22136233, compound

Product 1

HCID 22136231HCID 22136231, compound

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 4-(o-bromophenyl)-1-butanol (1.222 g, ca 0.0053 mol) and tetrakis(triphenylphosphine) palladium (0) (650 mg, 0.562 mmol) in 1,2-dimethoxyethane (55 mL) was added thiophene-2-boronic acid (2.057 g, 0.016 mol) and 1N aqueous NaHCO3 (15 mL). The resulting mixture was heated at reflux under nitrogen atmosphere for 3 days. The dark reaction mixture was diluted with water (50 mL) and extracted with EtOAc (100 mL). The organic layer was dried over Na2SO4, filtered through a bed of Celite and concentrated to yield a crude which was purified by flash chromatography (30% EtOAc in hexane) to yield 4-(2-thien-2-yl-phenyl)-butan-1-ol as a light brown oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux under nitrogen atmosphere for 3 days
  3. customThe dark reaction mixture
  4. extractionextracted with EtOAc (100 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered through a bed of Celite
  7. concentrationconcentrated
  8. customto yield a crude which
  9. customwas purified by flash chromatography (30% EtOAc in hexane)

Sources & evidence

ORD record
ord-92920d3160ed4878b70e0ffbf84db6e0
Source dataset
uspto-grants-2006_05
Patent number
US07053101B2

Reaction notes

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