1,2-Dimethoxyethane → HCID 22136239, compound

HRID 1836687Notes

Reaction equation

HRID 1836687 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9]C(OC)=O.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1B(O)O.[C:22]([O-:25])(O)=[O:23].[Na+].[CH3:27]OCCOC>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:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][C:3]=1[CH:8]([CH3:9])[C:22]([O:25][CH3:27])=[O:23]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 516892Sodium BicarbonateHCID 27339602-Thiopheneboronic acidHCID 15712815Methyl 3-(2-bromophenyl)propanoate

Product 1

HCID 22136239HCID 22136239, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

To a mixture of the crude methyl 3-(2-bromophenyl)propionate (1.59 g, ca 0.006 mol) and tetrakis(triphenylphosphine) palladium (0) (695 mg, 0.601 mmol) in 1,2-dimethoxyethane (45 mL) were added thiophene-2-boronic acid (2.304 g, 0.018 mol) and 1N aqueous NaHCO3 (15 mL). The resulting mixture was heated at reflux under nitrogen atmosphere for 66 hrs. The dark reaction mixture was then diluted with water (100 mL) and extracted with EtOAc (2×100 mL). The combined organic layers were dried over Na2SO4, filtered and then concentrated. The resulting crude product was purified by flash chromatography (5% EtOAc in hexane) to yield methyl 2-(2-thienyl)phenylpropionate as a light green oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux under nitrogen atmosphere for 66 hrs
  3. customThe dark reaction mixture
  4. extractionextracted with EtOAc (2×100 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting crude product was purified by flash chromatography (5% EtOAc in hexane)

Sources & evidence

ORD record
ord-5168b1a17ed6411bb08078ef0813ea48
Source dataset
uspto-grants-2004_08
Patent number
US06777421B2

Reaction notes

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