N-(1,3-di(prop-1-en-2-yl)dibenzo[b,d]furan-4-yl)acetamide → N-(1,3-diisopropyldibenzo[b,d]furan-4-yl)acetamide

HRID 1750919Notes

Reaction equation

HRID 1750919 reaction equation
[CH2:1]=[C:2]([C:4]1[C:12]2[C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[O:9][C:8]=2[C:7]([NH:17][C:18](=[O:20])[CH3:19])=[C:6]([C:21]([CH3:23])=[CH2:22])[CH:5]=1)[CH3:3]>C(O)C.[Pd].[Pt]>[CH:2]([C:4]1[C:12]2[C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[O:9][C:8]=2[C:7]([NH:17][C:18](=[O:20])[CH3:19])=[C:6]([CH:21]([CH3:23])[CH3:22])[CH:5]=1)([CH3:3])[CH3:1]

Participants

5

Reactant 1

HCID 58400985N-(1,3-di(prop-1-en-2-yl)dibenzo[b,d]furan-4-yl)acetamide

Product 1

HCID 58400954N-(1,3-diisopropyldibenzo[b,d]furan-4-yl)acetamideYield 82.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

In a 500 mL hydrogenation container was added N-(1,3-di(prop-1-en-2-yl)dibenzo[b,d]furan-4-yl)acetamide (22.6 g, 74.0 mmol), Pd/C, 10% (3 g, 74.0 mmol) and Pt/C, 5% (3 g, 74.0 mmol) in Ethanol (200 mL). After two days reaction, the solution was filtered through a Celite plug and washed with dichloromethane. The filtration was concentrated to give crude N-(1,3-diisopropyldibenzo[b,d]furan-4-yl)acetamide (18.8 g, 82% yield) as white solid.

Workup

  1. customAfter two days reaction
  2. filtrationthe solution was filtered through a Celite plug
  3. washwashed with dichloromethane
  4. filtrationThe filtration
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-675613fa777a4db7b0b4a347746992b2
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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