9-Borabicyclo(3.3.1)nonane → 4-Fluoro-2,3-dimethoxybenzene butanal
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]=[CH2:10])=[C:4]([O:11][CH3:12])[C:3]=1[O:13][CH3:14].B1C2CCCC1CCC2.[CH:24]([O:27][BH-](OC(C)C)OC(C)C)(C)C.[K+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH:24]=[O:27])=[C:4]([O:11][CH3:12])[C:3]=1[O:13][CH3:14]Participants
4
Procedure
The product from Example 54 (7.2 g) was treated with 9-BBN (85 ml, 0.5M in THF) at room temperature with stirring for 2 hours. The stirring was stopped and the reaction mixture cooled to 0° then potassium triisopropoxyborohydride (43 ml, 1.0M in THF) was added. Carbon monoxide was bubbled through the reaction mixture for 3 hours, then pH 7 buffer (60 ml) and 30% H2O2 (16 ml) was added with stirring and the reaction was allowed to stir overnight. The reaction mixture was quenched with water, and extracted with ethyl acetate. The organic layer was separated, dried and evaporated to afford the desired product as an oil.
Workup
- temperaturethe reaction mixture cooled to 0°
- customCarbon monoxide was bubbled through the reaction mixture for 3 hours
- additionpH 7 buffer (60 ml) and 30% H2O2 (16 ml) was added
- stirringwith stirring
- stirringto stir overnight
- customThe reaction mixture was quenched with water
- extractionextracted with ethyl acetate
- customThe organic layer was separated
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-fab4bad79380403093d4fd0a0286f3a2
- Source dataset
- uspto-grants-1987_01
- Patent number
- US04634705
Reaction notes
Loading…