1,2-Dimethoxyethane → 3-Vinyl-6,7-dihydro-[1,4]dioxino[2,3-c]pyridazine
Reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]2[O:8][CH2:9][CH2:10][O:11][C:4]=2[CH:3]=1.[CH2:12]([CH2:15]OC)OC>>[CH:12]([C:2]1[N:7]=[N:6][C:5]2[O:8][CH2:9][CH2:10][O:11][C:4]=2[CH:3]=1)=[CH2:15]Participants
Conditions
- Temperature
- 95 °C
Procedure
A solution of 3-chloro-6,7-dihydro[1,4]dioxino[2,3-c]pyridazine (13.6 g, 0.079 mol) containing ca. 15% of a bromo species in dimethoxyethane (400 ml) was degassed under argon for 10 min then tetrakis(triphenylphosphine)palladium (0) (2 g), potassium carbonate (10.33 g), 2,4,6-trivinylcyclotriboroxane pyridine complex (11.32 g) and water (55 ml) were added. The mixture was heated at 95° C. for 48 hours and cooled and evaporated to dryness. The mixture was treated with aqueous sodium bicarbonate solution and extracted (5×) with DCM. Extracts were dried (sodium sulphate), evaporated and the residue chromatographed on silica gel (500 g), eluting with 0-100% ethyl acetate-hexane, affording the product (6.43 g, 50%); [also some impure fractions (1.8 g)].
Workup
- customwas degassed under argon for 10 min
- additiontetrakis(triphenylphosphine)palladium (0) (2 g), potassium carbonate (10.33 g), 2,4,6-trivinylcyclotriboroxane pyridine complex (11.32 g) and water (55 ml) were added
- temperaturecooled
- customevaporated to dryness
- additionThe mixture was treated with aqueous sodium bicarbonate solution
- extractionextracted (5×) with DCM
- dry with materialExtracts were dried (sodium sulphate)
- customevaporated
- customthe residue chromatographed on silica gel (500 g)
- washeluting with 0-100% ethyl acetate-hexane
Sources & evidence
- ORD record
- ord-8cf104b74fbe4966997b310ecb1c448d
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732460B2
Reaction notes
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