4-(Prop-1-en-2-yl)dibenzo[b,d]furan → 4-Isopropyldibenzo[b,d]furan

HRID 717992Notes

Reaction equation

HRID 717992 reaction equation
[CH2:1]=[C:2]([C:4]1[C:9]2[O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH3:3]>[Pd].CCO>[CH:2]([C:4]1[C:9]2[O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:1]

Participants

4

Reactant 1

HCID 177536004-(Prop-1-en-2-yl)dibenzo[b,d]furan

Product 1

HCID 156919904-Isopropyldibenzo[b,d]furanYield 74.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(Prop-1-en-2-yl)dibenzo[b,d]furan (14.5 g, 69.6 mmol) was added to a hydrogenator bottle with EtOH (100 mL). The reaction mixture was degassed by bubbling N2 for 10 minutes. Pd/C (1.14 g, 1.39 mmol) and PVC (2.72 g, 0.7 mmol) was added. The reaction mixture was placed on a Parr hydrogenator for 2 hours (H2˜72 psi, based on calculations). The reaction mixture was filtered on a tightly packed Celite® bed and washed with dichloromethane. GC/MS confirmed complete conversion. The crude product was chromatographed on silica gel with 2% DCM in hexane (v/v) to yield 10.9 g (74%) of the desired product. The product was confirmed by GC/MS.

Workup

  1. customThe reaction mixture was degassed
  2. customby bubbling N2 for 10 minutes
  3. filtrationThe reaction mixture was filtered on a tightly packed Celite® bed
  4. washwashed with dichloromethane
  5. customThe crude product was chromatographed on silica gel with 2% DCM in hexane (v/v)

Sources & evidence

ORD record
ord-77501ad58e354d00ba752da7bacda49b
Source dataset
uspto-grants-2015_11
Patent number
US09193745B2

Reaction notes

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