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

HRID 238500Notes

Reaction equation

HRID 238500 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[OH:14])([O-:3])=[O:2].[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18]O.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.CCOC(C)=O>[C:10]([C:8]1[CH:7]=[CH:6][C:5]([O:14][CH2:18][CH2:17][N:16]([CH3:20])[CH3:15])=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=1)([CH3:11])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 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

To a mixture of 2-nitro-4-tert-butylphenol (2 g) and N,N-dimethylethanolamine (1.3 g) and PPh2 (4 g) in THF (50 ml) was added DEAD (2.6 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, was used in next step without further purification.

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-801b37de490b4ead84a0006f4ec8a71d
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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