Formaldehyde → Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine
Reaction equation
[CH2:1]=O.[CH2:3]([NH:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CO.[C:18](=[O:21])([O-])[O-].[K+].[K+]>CCOCC>[CH2:3]([N:10]([CH2:1][O:21][CH3:18])[CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
Into a round bottom 3-neck flask equipped with a nitrogen flow and a magnetic stirrer was added formaldehyde (74.000 mmol, 7.4000×10−2 mol) (as a 37% aqueous solution). The flask was cooled to 0° C. and N-benzyl-N-(trimethylsilyl)methylamine (10.000 g, 5.1716790×10−2 mol) was added dropwise with stirring. After stirring for 10 minutes at 0° C., methanol (6.000 mL, 0.14811874 mol) was added in one portion. Potassium carbonate (4.000 g, 2.8942408×10−2 mol) was added to the mixture to absorb the aqueous phase. The mixture was stirred for one hour, then the nonaqueous phase decanted, and then potassium carbonate (2.000 g, 1.4471204×10−2 mol) was added. The mixture was stirred at 25° C. for 12 hours. Ether is added to the mixture and the solution was dried over potassium carbonate, filtered and concentrated under reduced pressure. The residue is distilled at reduced pressure to give the product as a colorless liquid.
Workup
- customInto a round bottom 3-neck flask equipped with a nitrogen flow and a magnetic stirrer
- stirringAfter stirring for 10 minutes at 0° C.
- customto absorb the aqueous phase
- stirringThe mixture was stirred for one hour
- customthe nonaqueous phase decanted
- stirringThe mixture was stirred at 25° C. for 12 hours
- dry with materialthe solution was dried over potassium carbonate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- distillationThe residue is distilled at reduced pressure
Sources & evidence
- ORD record
- ord-d67aad925b52487fbd6feb2e222b12cc
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09126927B2
Reaction notes
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