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
3
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), triethenylboroxin pyridine complex (11.32 g) and water (55 ml) were added. The mixture was heated at 95° C. for 48 h 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), triethenylboroxin 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-bca3196f050e4950948142be4beab999
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709483B2
Reaction notes
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