2-Chloroethanol → 4-(2-chloroethoxy)-1H-indole
Reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:30][CH2:31][CH2:32]O.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Cl:30][CH2:31][CH2:32][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
To 2.0 g (1.5 mmol) 4-hydroxyindole in 50 mL THF at 0° C. is added 6.3 g (24 mmol) Ph3P, 1.51 mL (1.81 g, 22.53 mmol) 2-chloroethanol and 3.78 mL (4.19 g, 24.03 mmol) diethylazodicarboxylate. After stirring at 23° C. for 20 h, the dark reaction mixture is evaporated to a black oil. Diethyl ether (30 mL) is added, the dark solution stirred on a magnetic stir plate, and 200 mL hexanes is added (to precipitate Ph3PO). After stirring at 23° C. for 30 min, the mixture is filtered and the filtrate evaporated to a light yellow oil. Flash chromatography on SiO2 gel, eluting with hexanes/EtOAc (8/1 to 4/1), gives 1.13 g (5.78 mmol, a 39% yield) of the title compound as an off-white solid. MS (ES) m/z 196 (MH)+.
Workup
- customthe dark reaction mixture
- customis evaporated to a black oil
- additionDiethyl ether (30 mL) is added
- stirringthe dark solution stirred on a magnetic stir plate, and 200 mL hexanes
- additionis added (to precipitate Ph3PO)
- stirringAfter stirring at 23° C. for 30 min
- filtrationthe mixture is filtered
- customthe filtrate evaporated to a light yellow oil
- washFlash chromatography on SiO2 gel, eluting with hexanes/EtOAc (8/1 to 4/1)
- customgives 1.13 g (5.78 mmol
Sources & evidence
- ORD record
- ord-54ff67145a414987aae6ac97ed89ea7e
- Source dataset
- uspto-grants-2003_10
- Patent number
- US06632824B2
Reaction notes
Loading…