Methylamine → 3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-benzylidene-methyl-amine

HRID 1295731Notes

Reaction equation

[C:1]([Si:5]([CH3:19])([CH3:18])[O:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=O)([CH3:4])([CH3:3])[CH3:2].[CH3:20][NH2:21]>CCO>[C:1]([Si:5]([CH3:19])([CH3:18])[O:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[N:21][CH3:20])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-benzaldehyde (2.375 g, 8.47 mmol) was dissolved in 10 mL EtOH. MeNH2 (1.2 mL, 40% in H2O) was added and the mixture was heated to 40° C. for 30 min. The mixture was then concentrated in vacuo. The aqueous residue was diluted with isopropanol and then concentrated in vacuo. This was repeated twice more giving 2.184 g (87.89%) of a dry white powder.

Workup

concentrationThe mixture was then concentrated in vacuo
additionThe aqueous residue was diluted with isopropanol
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-cfa152d5c85340b7876cd666a0f794b6
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07244738B2

Reaction notes

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