Cesium carbonate → 2-(Biphenyl-4-ylmethoxy)ethanol

HRID 642969Notes

Reaction equation

HRID 642969 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[O:14]1[CH2:19]C[O:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.ClCCl.O>[C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:7][C:2]([CH2:19][O:14][CH2:15][CH2:16][OH:17])=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 163234-ChlorobiphenylHCID 312751,4-DioxaneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 592597172-(Biphenyl-4-ylmethoxy)ethanolYield 38%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 4-chlorobiphenyl (15 mg, 79.5 μmol) and 1,4-dioxane (1.5 ml) were added water (0.15 ml), cesium carbonate (117 mg, 358 μmol), sodium (2-hydroxyethoxy)methyl trifluoroborate (19.7 mg, 119 mol), palladium (II) acetate (5.37 mg, 23.9 μmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (19.6 mg, 47.7 μmol). Then, the reaction mixture was stirred at 100° C. (external temperature) for 13 hours. After the reaction mixture was cooled at room temperature, water and dichloromethane were added to the mixture, followed by filtration using Celite. The separated organic layer was washed with an aqueous saturated sodium chloride solution. The organic layer was separated, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1 NH silica gel) to obtain the title compound (6.8 mg, 30 μmol, 38%).

Workup

  1. temperatureAfter the reaction mixture was cooled at room temperature
  2. filtrationfollowed by filtration
  3. washThe separated organic layer was washed with an aqueous saturated sodium chloride solution
  4. customThe organic layer was separated
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1 NH silica gel)

Sources & evidence

ORD record
ord-07a8a06dd6fc425fa1da0ae6c20ad5c8
Source dataset
uspto-grants-2010_04
Patent number
US07696347B2

Reaction notes

Loading…