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

HRID 2292695Notes

Reaction equation

HRID 2292695 reaction equation
[C:1]([C:5]1[C:13]2S[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.CC[O:27]C(C)=O>CCO>[NH2:16][C:7]1[CH:6]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[C:13]2[O:27][CH2:11][C:10]([CH3:14])([CH3:15])[C:9]=2[CH:8]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 21479418HCID 21479418, compound

Product 1

HCID 106804065-Amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 7-tert-butyl-2,3-dihydro-3,3-dimethyl-5-nitro-benzothiophene (2.6 g, 8.8 mmol) 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, which is used without further purification.

Workup

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

Sources & evidence

ORD record
ord-b58b2a660dda4a8cbd57093bccd6efe8
Source dataset
uspto-grants-1997_11
Patent number
US05684041

Reaction notes

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