Pentamethyldiethylenetriamine → HCID 86617925, compound
Reaction equation
[CH3:1][O:2][CH:3]([O:13][CH3:14])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[F:12].CN(CCN(CCN(C)C)C)C.C([Li])CCC.[CH:32](N1CCOCC1)=[O:33]>O.C1COCC1>[CH3:14][O:13][CH:3]([O:2][CH3:1])[C:4]1[C:5]([F:12])=[C:6]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH:32]=[O:33]Participants
Conditions
- Temperature
- -60 °C
Procedure
To 15 ml of a THF solution containing 3.665 g of 2-dimethoxymethyl-1-fluoro-4-methoxybenzene [CAS No. 883576-30-5] and 3.48 g of N,N,N′,N′,N″-pentamethyldiethylenetriamine, 7.1 ml of n-butyllithium (2.66 M, hexane solution) was added dropwise at −74° C. The resulting mixture was stirred at −60° C. for 3 hours, and then 3 ml of N-formylmorpholine was added thereto. The temperature of the reaction mixture was slowly allowed to rise to room temperature. Then, water was added to the reaction mixture while cooling on ice, and then the mixture was extracted with a mixture of hexane and t-butylmethyl ether and dried over anhydrous magnesium sulfate. The desiccating agent was removed by filtration, and the filtrate was concentrated under reduced pressure to give a crude product of 3-dimethoxymethyl-2-fluoro-5-methoxybenzaldehyde.
Workup
- customto rise to room temperature
- temperaturewhile cooling on ice
- extractionthe mixture was extracted with a mixture of hexane and t-butylmethyl ether
- dry with materialdried over anhydrous magnesium sulfate
- customThe desiccating agent was removed by filtration
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-00253a9eba1b49a3bedb0ce6f69c97fd
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07816522B2
Reaction notes
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