Toluene → HCID 67515608, compound

HRID 2173139Notes

Reaction equation

HRID 2173139 reaction equation
Br[C:2]1[C:3]([CH3:13])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][CH2:6][CH2:5]2.[CH2:14]([Sn](CCCC)(CCCC)CCCC)[CH:15]=[CH2:16].[Cl-].[Li+].C1(C)C=CC=CC=1>CCOC(C)=O.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>[CH3:13][C:3]1[C:2]([CH2:16][CH:15]=[CH2:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][O:7][C:8]2=[O:12]

Participants

7

Reactant 4

HCID 1140TolueneHCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 67517345HCID 67517345, compound

Product 1

HCID 67515608HCID 67515608, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a flask charged with 6-Bromo-5-methyl-3,4-dihydro-1H-isochromen-1-one (100 mg, 0.42 mmol), Allyl Tri-n-butyltin (165 mg, 0.50 mmol), Palladium Tetrakis (48 mg, 0.041 mmol), and Lithium Chloride (35 mg, 0.83 mmol) was added Toluene (5 ml). The mixture was sealed with a condenser and purged three times with N2. The mixture was then heated to reflux for 6 hours. TLC and LC showed complete reaction. The reaction was diluted with EtOAc (50 mL), washed with brine, dried over sodium sulfate, adsorbed onto silica, and purified by MPLC (Hex/EtOAc gradient) to furnish the product. LC-MS (IE, m/z): 203 [M+1]+.

Workup

  1. customThe mixture was sealed with a condenser
  2. custompurged three times with N2
  3. temperatureThe mixture was then heated
  4. temperatureto reflux for 6 hours
  5. customreaction
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. custompurified by MPLC (Hex/EtOAc gradient)
  9. customto furnish the product

Sources & evidence

ORD record
ord-f27c58c7754f4319a4a11799f52d97c7
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…