Sodium Carbonate → HCID 22002654, compound

HRID 325184Notes

Reaction equation

HRID 325184 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:6][C:5](=[O:7])[C:4](I)=[CH:3]1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:9])[CH2:6][C:5](=[O:7])[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:3]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 11773TriphenylarsineHCID 66827Phenylboronic AcidHCID 22002644HCID 22002644, compound

Product 1

HCID 22002654HCID 22002654, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

A 250 mL round bottom flask was charged with 4,4-dimethyl-2-iodo-2-cyclopenten-1-one from Step 1 (1.59 g, 6.7 mmol), bis(benzontrile)-palladium(II) chloride (235 mg, 0.61 mmol), phenylboronic acid (983 mg, 8.1 mmol), triphenylarsine (308 mg, 1.0 mmol), 2.0 M Na2CO3 (8.4 mL, 16.8 mmol) and benzene (70 mL). The reaction flask was well purged with nitrogen and the reaction was stirred at 80° C. for 2.5 h. The reaction was allowed to cool to r.t., diluted with NH4OAc buffer 25% w/v (100 mL) and extracted with EtOAc. The organic extract was dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash chromatography eluting with 10% EtOAc in hexane to give the title compound as a light yellow syrup.

Workup

  1. customThe reaction flask was well purged with nitrogen
  2. temperatureto cool to r.t.
  3. additiondiluted with NH4OAc buffer 25% w/v (100 mL)
  4. extractionextracted with EtOAc
  5. extractionThe organic extract
  6. dry with materialwas dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography
  9. washeluting with 10% EtOAc in hexane

Sources & evidence

ORD record
ord-01f0087046884a23b219500f59cab8ab
Source dataset
uspto-grants-2001_04
Patent number
US06222048B1

Reaction notes

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