Toluene → HCID 77230673, compound

HRID 2173182Notes

Reaction equation

HRID 2173182 reaction equation
Br[C:2]1[CH:11]=[C:10]([CH3:12])[C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=1.C([Sn](CCCC)(CCCC)CCCC)C=C.[Cl-].[Li+].C1(C)C=CC=CC=1.[CH3:38][CH2:39][O:40]C(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>[CH3:12][C:10]1[C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=[C:2]([CH2:38][CH:39]=[O:40])[CH:11]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 53311242HCID 53311242, compound

Product 1

HCID 77230673HCID 77230673, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a flask charged with 5-bromo-7-methyl-2-benzofuran-1(3H)-one (27 mg, 0.12 mmol) and a stir bar was added allyl tri-n-butyltin (79 mg, 0.24 mmol), lithium chloride (15 mg, 0.36 mmol), palladium tetrakis (28 mg, 0.024 mmol), and toluene (4 mL). The reaction was sealed with a condensor, purged three times with nitrogen, and heated to reflux for 16 hours. LC showed good reaction at that point. The reaction was diluted with EtOAc, adsorbed onto silica gel, and purified by flash chromatography. Removal of solvent gave rise to (7-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde as a light yellow oil. LC/MS: (IE, m/z) (M+1)+=189.2.

Workup

  1. customThe reaction was sealed with a condensor
  2. custompurged three times with nitrogen
  3. temperatureheated
  4. temperatureto reflux for 16 hours
  5. customreaction at that point
  6. custompurified by flash chromatography
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-bc7e48e980c24db9907a70410499b28a
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…