Triphenylphosphine → 2-(2-Pyrrolidin-1-ylethoxy)-4-nitroanisole
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].[N:13]1([CH2:18][CH2:19]O)[CH2:17][CH2:16][CH2:15][CH2:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>>[N:13]1([CH2:18][CH2:19][O:12][C:4]2[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:17][CH2:16][CH2:15][CH2:14]1Participants
Procedure
A stirred solution of 2-methoxy-5-nitrophenol (1.5 g, 0.0088 mole), 1-pyrrolidineethanol (1.03 ml, 0.0088 mole) and triphenylphosphine (2.4 g, 0.0088 mole) in TBF (50 ml) at room temperature under argon was treated with diethyl azodicarboxylate (1.4 ml, 0.0088 mole). The reaction mixture was stirred for 1 h, then concentrated in vacuo and the residue treated with 2M HCl acid (50 ml) and ethyl acetate (50 ml). The mixture was shaken well, then the acid layer separated, washed with ethyl acetate (2×30 ml) and then basified by addition of potassium carbonate. The basic mixture was extracted with ethyl acetate (2×50 ml) and the combined extract dried (Na2SO4) and concentrated in vacuo to afford the title compound as a yellow oil (1.43 g, 61%).
Workup
- concentrationconcentrated in vacuo
- additionthe residue treated with 2M HCl acid (50 ml) and ethyl acetate (50 ml)
- stirringThe mixture was shaken well
- customthe acid layer separated
- washwashed with ethyl acetate (2×30 ml)
- additionbasified by addition of potassium carbonate
- extractionThe basic mixture was extracted with ethyl acetate (2×50 ml)
- extractionthe combined extract
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c72df319ed2a4330a0725ecd841b1da0
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05801170
Reaction notes
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