Hexane → 5-Amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran

HRID 2292689Notes

Reaction equation

HRID 2292689 reaction equation
[C:1]([C:5]1[C:13]2[O:12][CH2:11][C:10]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([N+:16]([O-])=O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCCCCC.CCOC(C)=O>[Pd].CCO>[NH2:16][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:13]2[O:12][CH2:11][C:10]([CH3:14])([CH3:15])[C:9]=2[CH:8]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 107531427-tert-Butyl-2,3-dihydro-3,3-dimethyl-5-nitro-benzofuran

Product 1

HCID 106804065-Amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuranYield 88.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 7-tert-butyl-2,3-dihydro-3,3-dimethyl-5-nitro-benzofuran (2.2 g, 8.8 mmol) and 10% palladium on carbon (200 mg) in absolute EtOH (60 mL) is hydrogenated at 40 psi of H2 pressure on a Parr hydrogenation apparatus for 3 h at 22° C. The reaction is judged complete by TLC (hexane:EtOAc, 19:1; visualized with Dragendorff reagent). The reaction mixture is filtered through Celite and evaporated to yield the title compound as a purple solid (1.7 g, 88%), which is used without further purification.

Workup

  1. filtrationThe reaction mixture is filtered through Celite
  2. customevaporated

Sources & evidence

ORD record
ord-db63a931f3f943c89666b1b2661fd27f
Source dataset
uspto-grants-1997_11
Patent number
US05684041

Reaction notes

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