Sodium Carbonate → HCID 58662614, compound

HRID 1181596Notes

Reaction equation

HRID 1181596 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][CH2:11][C@H:12]1[CH2:14][O:13]1)[CH3:9].C(=O)([O-])[O-].[Na+].[Na+].[C:21]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)#[N:22]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:13]1[CH2:14][C@@H:12]1[CH2:11][O:10][CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:26]1[CH:27]=[CH:28][C:23]([C:21]#[N:22])=[CH:24][CH:25]=1)[CH3:9]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 86605594HCID 86605594, compound

Product 1

HCID 58662614HCID 58662614, compoundYield 26.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

(R)-2-[1-(2-Bromophenyl)ethoxymethyl]oxirane (8.24 g) was dissolved in toluene (38 ml) and ethanol (150 ml), 2M-aqueous sodium carbonate (80 ml), 4-cyanophenylboronic acid (5.65 g) and tetrakis(triphenylphosphine)palladium(0) (1.85 g) were successively added, and the mixture was heated under reflux overnight. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. Water was added to the obtained residue, and the mixture was extracted 3 times with diethyl ether. The organic layer was washed successively with water and brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1) to give the title compound (2.40 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. additionWater was added to the obtained residue
  5. extractionthe mixture was extracted 3 times with diethyl ether
  6. washThe organic layer was washed successively with water and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-05e8a7cbf08f48cd92d7fe6c2d8c90ae
Source dataset
uspto-grants-2007_10
Patent number
US07285572B2

Reaction notes

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