Formaldehyde → HCID 57864762, compound

HRID 2425529Notes

Reaction equation

[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:8][CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]=O.CO.[C:24]([O-:27])([O-])=O.[K+].[K+]>O.CC(OC)(C)C>[CH3:20][O:27][CH2:24][N:8]([CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Diphenyl-N-((trimethylsilyl)methyl)methanamine (5.5 g, 20.4 mmol) was added dropwise to mixture of 37% aqueous formaldehyde (2.9 g) and methanol (1.5 g) while stirring at 0° C. After the addition was complete the reaction mixture was stirred for 2 hours at 0° C. K2CO3 (3 g) was added and the solidified mixture was warmed to room temperature. Methanol (4 ml) was added. After one hour stirring at room temperature, tBME (50 ml) and water (5 ml) was added. The organic layer was separated and dried with Na2SO4. Evaporation under vacuum gave the crude product N-(methoxymethyl)diphenyl-N-((trimethylsilyl)methyl)methanamine (7.05 g, max. 20.4 mmol) as an oil, which solidified on standing overnight at room temperature. The product was used without further purification.

Workup

additionAfter the addition
stirringwas stirred for 2 hours at 0° C
temperaturethe solidified mixture was warmed to room temperature
stirringAfter one hour stirring at room temperature
customThe organic layer was separated
dry with materialdried with Na2SO4
customEvaporation under vacuum

Sources & evidence

ORD record: ord-20427ba3664e49c191b5d4496b33f5b2
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964739B2

Reaction notes

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