1,2-Dimethoxyethane → 1-(2'-(Benzyloxy)-3'-phenylbiphenyl-3-yl)ethanone

HRID 45469Notes

Reaction equation

HRID 45469 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1)(=O)=O.[C:29]([C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1)(=[O:31])[CH3:30].C(COC)OC.C(=O)(O)[O-].[Na+]>O.[Pd].C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:20]([O:19][C:8]1[C:9]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:10][CH:11]=[CH:12][C:7]=1[C:36]1[CH:35]=[CH:34][CH:33]=[C:32]([C:29](=[O:31])[CH3:30])[CH:37]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

9

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 516892Sodium BicarbonateHCID 27343103-Acetylphenylboronic acidHCID 582385672-(Benzyloxy)biphenyl-3-yl trifluoromethanesulfonate

Product 1

HCID 582385951-(2'-(Benzyloxy)-3'-phenylbiphenyl-3-yl)ethanoneYield 100%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 31 (3.18 g, 7.8 mmol), 3-acetylphenylboronic acid (1.6 g, 9.76 mmol, 1.25 equiv.), glyme (5 mL), bis(triphenylphosphine)palladium(II) dichloride (25 mg) and sodium bicarbonate (2.1 g) in water (40 mL) was kept at reflux under nitrogen for 11 hr with additional palladium catalyst (2×30 mg) added after 3 and 7 hr. After cooling, the reaction mixture was diluted with ethyl acetate (200 mL) and washed with water (2×800 mL). The organic layer was dried over sodium sulfate and filtered. The solvent was removed in a rotary evaporator and the crude product was purified by chromatography on silica (120 g) with 2% ethyl acetate in heptane (4 L) to afford 32 (2.9 g, 100%).

Workup

  1. additionadded after 3 and 7 hr
  2. temperatureAfter cooling
  3. washwashed with water (2×800 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed in a rotary evaporator
  7. customthe crude product was purified by chromatography on silica (120 g) with 2% ethyl acetate in heptane (4 L)

Sources & evidence

ORD record
ord-0f16a94773714b63b0a4c8cdcdc0b2f2
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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