Sodium Bicarbonate → HCID 22022226, compound

HRID 1827280Notes

Reaction equation

HRID 1827280 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][OH:6].[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]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:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][OH:6]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 27339602-Thiopheneboronic acidHCID 27340892-(2-Bromophenyl)ethan-1-ol

Product 1

HCID 22022226HCID 22022226, compound

Reagents, catalysts & solvents 3

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

Procedure

To a stirring mixture of 2-bromophenethyl alcohol (0.72 mL, 5.31 mmol) and tetrakis (triphenylphosphine) palladium (0) (620 mg, 10 mol %) in 1,2-dimethoxyethane (45 mL) was added thiophene-2-boronic acid. (2.0391 g, 0.0159 mol) and 1N aqueous NaHCO3 (15 mL). The resultant reaction mixture was heated at reflux for 66 h under argon atmosphere. The dark reaction mixture was diluted with H2O (20 mL) and extracted with EtOAc (2×75 mL). The organic solution was dried over Na2SO4, filtered and concentrated. The dark residue was purified by flash chromatography on silica gel (30% EtOAc in hexane) to yield 2-(2-thienyl)phenethyl alcohol as a light yellow oil.

Workup

  1. customThe resultant reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 66 h under argon atmosphere
  4. customThe dark reaction mixture
  5. extractionextracted with EtOAc (2×75 mL)
  6. dry with materialThe organic solution was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe dark residue was purified by flash chromatography on silica gel (30% EtOAc in hexane)

Sources & evidence

ORD record
ord-b7aa346324ec4c1bbc54f918cf599d70
Source dataset
uspto-grants-2006_05
Patent number
US07053101B2

Reaction notes

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