Hydroxide → HCID 1736026, compound

HRID 1669917Notes

Reaction equation

HRID 1669917 reaction equation
[OH-:1].[C:2]1(/[CH:8]=[CH:9]/B(O)O)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>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>[CH:9](/[C:4]1[CH:5]=[CH:6][C:7]2[O:1][C:9]3[CH:4]=[CH:3][C:2](/[CH:9]=[CH:8]/[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:7][C:8]=3[C:2]=2[CH:3]=1)=[CH:8]\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 961HydroxideHCID 5702628Styrylboronic acid

Product 1

HCID 1736026HCID 1736026, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Tetrethylamine hydroxide (13.6 g, 18.4 mmol), tetrakis(triphenylphosphine)palladium(0) (142 mg) and trans-2-phenylvinylboronic acid (2.3 g, 15.3 mmol) are added to a solution of the product from example 1a) (2.00 g, 6.14 mmol) in N,N′-Dimethylacetamide (DMA) (30 ml). The mixture is then stirred at 110° C. for 24 hours. The reaction mixture is cooled to room temperature and poured into H2O. A gray crude product is obtained after filtration and washing with n-hexane. The crude product is purified by silicagel column chromatography with CH2Cl2, which result in a white solid (71% yield, mp.: 226° C.).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customA gray crude product is obtained
  3. filtrationafter filtration
  4. washwashing with n-hexane
  5. customThe crude product is purified by silicagel column chromatography with CH2Cl2, which

Sources & evidence

ORD record
ord-1535b1bc1fcf4101bde511043767328d
Source dataset
uspto-grants-2011_08
Patent number
US07989644B2

Reaction notes

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