2-(Dimethylamino)ethanol → (2-[4-(Tert-butyl)-2-nitrophenoxy]-ethyl)dimethylamine

HRID 2211635Notes

Reaction equation

HRID 2211635 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[N+:13]([C:16]1[CH:21]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:19]=[CH:18][C:17]=1[OH:26])([O-:15])=[O:14].[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.CCOC(C)=O>[C:22]([C:20]1[CH:19]=[CH:18][C:17]([O:26][CH2:30][CH2:29][N:28]([CH3:32])[CH3:27])=[C:16]([N+:13]([O-:15])=[O:14])[CH:21]=1)([CH3:23])([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 18661Phenol, 4-(1,1-dimethylethyl)-2-nitro-HCID 5462977Diethyl azodicarboxylate

Product 1

HCID 21959559(2-[4-(Tert-butyl)-2-nitrophenoxy]-ethyl)dimethylamine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

DEAD (2.6 mL) was added to a mixture of 2-nitro-4-tert-butylphenol (2 g) and N,N-dimethylethanolamine (1.3 g) and Ph3P (4 g) in THF (50 mL). The reaction was stirred at RT for 1 h, diluted with EtOAc (50 mL) and washed with 1 N HCl twice. The aqueous layer was basified with NaHCO3, extracted with EtOAc twice and washed with H2O and brine. The organic layer was dried over Na2SO4 and evaporated to give (2-[4-(tert-butyl)-2-nitrophenoxy]ethyl)-dimethylamine. It was hydrogenated under H2 atmosphere to give {2-[4-(tert-butyl)-2-aminophenoxy]ethyl}-dimethylamine.

Workup

  1. washwashed with 1 N HCl twice
  2. extractionextracted with EtOAc twice
  3. washwashed with H2O and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-e72854722fac4f74b1b5d736b7027134
Source dataset
uspto-grants-2006_09
Patent number
US07101868B2

Reaction notes

Loading…