Chloroform → 5-(2,2-dichlorovinyl)-2,2,8-trimethyl-4H-1,3-dioxino[4,5-c]pyridine
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[K+].[CH:26]([Cl:29])(Cl)[Cl:27].[CH3:30][C:31]1([CH3:44])[O:43][C:35]2[C:36]([CH3:42])=[N:37][CH:38]=[C:39]([CH:40]=O)[C:34]=2[CH2:33][O:32]1>CCCCCCC>[Cl:27][C:26]([Cl:29])=[CH:40][C:39]1[CH:38]=[N:37][C:36]([CH3:42])=[C:35]2[O:43][C:31]([CH3:44])([CH3:30])[O:32][CH2:33][C:34]=12Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a well stirred ice-cooled mixture of 0.1 mole of triphenylphosphine and 0.1 mole of potassium t-butoxide in 250 ml. of heptane is added over thirty minutes a mixture of 0.1 mole of chloroform in 200 ml. of heptane. The resulting mixture is concentrated in vacuo at 15°-20° to a volume of about 100 ml. and a solution of 0.1 mole of 2,2,8-trimethyl-4H-1,3-dioxino[4,5-c]-pyridine-5-carboxaldehyde in 250 ml. of heptane is added. The reaction mixture was heated at 40°-50° for 5 hours, then cooled, filtered, and concentrated in vacuo to give crude product. Chromatography on silica gel and elution with ether-petroleum ether (10-50%) gives pure 5-(2,2-dichlorovinyl)-2,2,8-trimethyl-4H-1,3-dioxino[4,5-c]pyridine.
Workup
- temperatureTo a well stirred ice-cooled
- concentrationThe resulting mixture is concentrated in vacuo at 15°-20° to a volume of about 100 ml
- temperatureThe reaction mixture was heated at 40°-50° for 5 hours
- temperaturecooled
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto give crude product
- washChromatography on silica gel and elution with ether-petroleum ether (10-50%)
Sources & evidence
- ORD record
- ord-57e128a5a6c94a6084ef94f74f74c847
- Source dataset
- uspto-grants-1985_10
- Patent number
- US04546106
Reaction notes
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