Triethylamine → HCID 117843342, compound

HRID 2209300Notes

Reaction equation

HRID 2209300 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([O:9][CH2:10][C:11]([CH3:13])=[CH2:12])[CH:3]=1.C([O-])=O.[Na+].CCN(CC)CC>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.O.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[C:11]([CH3:13])([CH3:12])[CH2:10][O:9][C:4]=2[CH:3]=1

Participants

9

Reactant 3

HCID 8471TriethylamineHCID 2723810Sodium FormateHCID 117843048HCID 117843048, compound

Product 1

HCID 117843342HCID 117843342, compoundYield 58%

Reagents, catalysts & solvents 5

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-chloro-1-iodo-2-((2-methylallyl)oxy)benzene (160 mg, 0.519 mmol), sodium formate (35.3 mg, 0.519 mmol), tetrabutylammonium chloride (144 mg, 0.519 mmol), and Pd(OAc)2 (23.3 mg, 0.104 mmol) in degassed DMF (1.5 mL) was added Et3N (0.181 ml, 1.30 mmol) and the reaction was heated to 80° C. After 1 hour, the reaction was cooled, diluted with water and EtOAc, the layers were separated, and the aqueous layer was extracted with EtOAc (1x). The organic layer was dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography (5-20% EtOAc in hexanes) to afford 6-chloro-3,3-dimethyl-2,3-dihydrobenzofuran 7.48 (55 mg).

Workup

  1. temperaturethe reaction was cooled
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (1x)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (5-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d5c4f46fe54c4d5fae9ce7f282617982
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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