Water → 5-Cyano-2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran
Reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH:9]([OH:11])[C:8]([CH3:13])([CH3:12])[C:7]=2[CH:14]=1)#[N:2].[CH2:15](N(CC)CC)[CH3:16].O.C(OCC)C>C(O)C.S(=O)(=O)(O)O>[CH3:13][C:8]1([CH3:12])[C:7]2[CH:14]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=2[O:10][CH:9]1[O:11][CH2:15][CH3:16]Participants
7
Procedure
The product of stage (b) (32.2 g) was boiled under reflux in ethanol (200 ml) containing sulphuric acid (7 drops) for 2 hours. The solution was cooled, neutralised with triethylamine and reduced to half volume under vacuum. Addition to water and isolation through diethyl ether gave 34.4 g of crude title product as a yellow oil. This was dissolved in petroleum ether bp 40°-60° C. containing 5% diethyl ether, then filtered through a bed of aluminium oxide followed by elution with the same solvent mixture. This yielded 30.5 g of the pure product as a colourless oil.
Workup
- temperatureThe solution was cooled
Sources & evidence
- ORD record
- ord-9c07da3c45f740b4b42d22325cd2ba16
- Source dataset
- uspto-grants-1982_06
- Patent number
- US04333759
Reaction notes
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