Dimethylformamide → 5-(1,1-Dimethyl-allyl)-2-methoxy-benzaldehyde
Reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:12])([CH3:11])[CH:9]=[CH2:10])[CH:5]=[CH:4][C:3]=1[O:13][CH3:14].[Li]CCCC.CN([CH:23]=[O:24])C>C1COCC1>[CH3:11][C:8]([C:6]1[CH:5]=[CH:4][C:3]([O:13][CH3:14])=[C:2]([CH:7]=1)[CH:23]=[O:24])([CH3:12])[CH:9]=[CH2:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 2-Bromo-4-(1,1-dimethyl-allyl)-1-methoxy-benzene (3.1 g, 0.012 mol) in dry THF (50 mL) was cooled to −78° C. under argon. n-BuLi (2.5M, 5.1 mL, 0.0128 mol) was added keeping the temperature below −70° C. The yellow mixture was stirred for another 15 min and quenched with dry DMF (1.4 mL, 0.018 mol). The cooling bath was removed and the mixture was allowed to warm to 25° C. A saturated solution of NaHCO3 (30 mL) was added and then extracted with EtOAc (3×50 mL). The organic phase was dried (Na2SO4) and evaporated to yellow oil. Yield: 2.31 g (94%).
Workup
- customthe temperature below −70° C
- customThe cooling bath was removed
- additionA saturated solution of NaHCO3 (30 mL) was added
- extractionextracted with EtOAc (3×50 mL)
- dry with materialThe organic phase was dried (Na2SO4)
- customevaporated to yellow oil
Sources & evidence
- ORD record
- ord-ada405e7b3eb4dd8838b9f85449f6475
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07642367B2
Reaction notes
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