Ethyl Acetate → HCID 68413903, compound
Reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([O:10][CH:11]2[CH2:16][NH:15][CH2:14][C:13]3[O:17][CH:18]=[CH:19][C:12]2=3)[CH:6]=[CH:7][C:8]=1[Cl:9].I[CH2:21][CH2:22][OH:23].C(OCC)(=O)C.C(OC(=O)C)C.Cl>C(O)C>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]([O:10][CH:11]2[CH2:16][N:15]([CH2:21][CH2:22][OH:23])[CH2:14][C:13]3[O:17][CH:18]=[CH:19][C:12]2=3)[CH:6]=[CH:7][C:8]=1[Cl:9]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
4-(3,4-Dichlorophenyloxy)-4,5,6,7-tetrahydrofuro-[2,3-c]pyridine hydrochloride (Example 119) (50 mg) was dissolved in 5 mL of dehydrated ethanol and then 220 mg of 2-iodoethanol was dropped thereinto. The reaction solution was heated with stirring at 80° C. overnight and concentrated in vacuo to evaporate the solvent and excess 2-iodoethanol. The residue was purified by silica gel column chromatography and the resulting free substance of the objective compound was dissolved in 5 mL of ethyl acetate. Into this ethyl acetate solution was dropped a solution of one equivalent of hydrochloric acid ethyl acetate and the resulting mixed solution was concentrated to give 18 mg of the objective compound.
Workup
- temperatureThe reaction solution was heated
- concentrationconcentrated in vacuo
- customto evaporate the solvent and excess 2-iodoethanol
- customThe residue was purified by silica gel column chromatography
- dissolutionthe resulting free substance of the objective compound was dissolved in 5 mL of ethyl acetate
- additionthe resulting mixed solution
- concentrationwas concentrated
Sources & evidence
- ORD record
- ord-11dbf156909e45e5af88321a89f529b1
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08217031B2
Reaction notes
Loading…