Sodium hydride → HCID 12661867, compound
Reaction equation
C(CP(=O)([O:8][CH2:9][CH3:10])OCC)#N.[H-].[Na+].[Cl:14][C:15]1[C:23]([CH:24]=O)=[C:19]2[CH:20]=[CH:21][O:22][C:18]2=[CH:17][CH:16]=1.ClC1C(C=O)=CC2[O:34][CH:33]=[CH:32]C=2C=1>COCCOC>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([O:22][CH2:21][CH:20]([O:8][CH2:9][CH3:10])[O:34][CH2:33][CH3:32])=[CH:19][C:23]=1[CH3:24]Participants
Procedure
A solution of diethyl cyanomethylphosphonate (11.5 ml) in dry ethylene glycol dimethyl ether (DME; 10 ml) was added dropwise to a suspension of sodium hydride (60%; 2.914 g) in DME (50 ml) at 0° under nitrogen. The mixture was stirred at 0° for 20 mins. Then a solution of 5-chloro-benzofuran-4-carbaldehyde mixture with 5-chloro-benzofuran-6-carbaldehyde (10.95 g) in DME (50 ml) was added in one portion. The mixture was heated at 60° for 2 h, cooled to room temperature and partitioned between water (150 ml) and ether (3×100 ml). The combined organic extracts were washed with brine (2×100 ml) and dried (MgSO4). The solvent was evaporated and the residue purified by column chromatography. Elution with cyclohexane/ethyl acetate 20:1 gave the title compound as a colourless solid (6.75 g)
Workup
- temperatureThe mixture was heated at 60° for 2 h
- custompartitioned between water (150 ml) and ether (3×100 ml)
- washThe combined organic extracts were washed with brine (2×100 ml)
- dry with materialdried (MgSO4)
- customThe solvent was evaporated
- customthe residue purified by column chromatography
- washElution with cyclohexane/ethyl acetate 20:1
Sources & evidence
- ORD record
- ord-5c5f99e1bddb4f62bcf5c00752306dd5
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05981572
Reaction notes
Loading…