Triethylamine → HCID 12018137, compound
Reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[C:11](Cl)(=O)[C:12](Cl)=[O:13].C(N(CC)CC)C.[Cl:24][CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:30]=[C:31]([CH2:35][C:36]([OH:38])=[O:37])[CH:32]=[CH:33][CH:34]=1>C(OCC)C.ClCCl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:13])[O:37][C:36](=[O:38])[C:35]=2[C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([O:28][CH2:27][CH2:26][CH2:25][Cl:24])[CH:30]=2)=[CH:3]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of N-methylindole (1.16 mL, 9.1 mmol) in diethyl ether (70 mL) at 0° C. was added dropwise oxalyl chloride (0.83 mL, 1.1 eq.). After the additon, the reaction mixture was stirred at 0° C. for 15 min., and the volatiles were removed under vacuo. The residue was re-dissolved in dichloromethane (70 mL) and triethylamine (2.3 mL, 2 eq.) was added. The reaction mixture was cooled to 0° C. and a solution of 3-(3-chloro-propyloxy)phenylacetic acid (2.73 g, 10 mmol) in dichloromethane (70 mL) was added dropwise. The resulting mixture was stirred at 0° C., and then allowed to warm up to room temperature overnight. Volatiles were removed under vacuo and the residue was purified on a silica gel column with dichloromethane to give 3-(1-methylindol-3-yl)-4-[3-(3-chloropropyloxy)phenyl]furan-2,5-dione (1.1 g).
Workup
- customthe volatiles were removed under vacuo
- dissolutionThe residue was re-dissolved in dichloromethane (70 mL)
- temperatureThe reaction mixture was cooled to 0° C.
- stirringThe resulting mixture was stirred at 0° C.
- temperatureto warm up to room temperature overnight
- customVolatiles were removed under vacuo
- customthe residue was purified on a silica gel column with dichloromethane
Sources & evidence
- ORD record
- ord-09a1e1f3fbc9453c8599c328f463fa65
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479490B2
Reaction notes
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