1,2-Dimethoxyethane → HCID 86652859, compound

HRID 45445

Reaction equation

HRID 45445 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:8]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=O)=O.[CH:27]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)=[O:28].C(COC)OC.C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C.[Pd](Cl)Cl.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>[CH2:18]([O:17][C:8]1[C:9]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:10][CH:11]=[CH:12][C:7]=1[C:33]1[CH:32]=[CH:31][CH:30]=[C:29]([CH:27]=[O:28])[CH:34]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 516892Sodium BicarbonateHCID 27343563-Formylphenylboronic acidHCID 58238569HCID 58238569, compound

Product 1

HCID 86652859HCID 86652859, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 8 (3.75 g, 9.65 mmol), 3-formylphenylboronic acid (2.89 g, 19.3 mmol, 2 equiv.), bis(triphenylphosphine) palladium(II) dichloride (0.20 g), glyme (10 mL) and a solution of sodium bicarbonate (2.9 g, 34.5 mmol) in water (50 mL) was stirred well at reflux under nitrogen for 4 hr. After cooling the reaction mixture was diluted with ethyl acetate (150 mL) and washed with water (2×100 mL). The organic layer was dried over sodium sulfate and filtered. The solvent was removed in a rotary evaporator. The crude product was purified by chromatography on silica (120 g) with heptane (3 L) to afford pure 9 (3.19 g, 99%).

Workup

  1. temperatureat reflux under nitrogen for 4 hr
  2. temperatureAfter cooling the reaction mixture
  3. washwashed with water (2×100 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 heptane (3 L)

Sources & evidence

ORD record
ord-f7650247cf4c4e9c8c6415d233b00d00
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Linked notes

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