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

HRID 2109612Notes

Reaction equation

HRID 2109612 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-d488a1c93cf6485caf3f072ffab0951d
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

Loading…