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

HRID 2247259Notes

Reaction equation

HRID 2247259 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.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.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

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

To a mixture of 2-nitro-4-tert-butylphenol (2 g) and N,N-dimethylethanolamine (1.3 g) and PPh3 (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-54221537a8fa4d239f331b3c74ee96ae
Source dataset
uspto-grants-2010_03
Patent number
US07687643B2

Reaction notes

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