Diethyl Ether → HCID 20187649, compound

HRID 2308805Notes

Reaction equation

[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].Br[C:7]1[CH:8]=[C:9]([CH:19]=[CH:20][CH:21]=1)[N:10]([Si:15]([CH3:18])([CH3:17])[CH3:16])[Si:11]([CH3:14])([CH3:13])[CH3:12].CCO[CH2:25][CH3:26].Cl[Si:28]([CH3:35])([CH3:34])[O:29][Si:30](Cl)([CH3:32])[CH3:31]>CCCCCC>[CH3:12][Si:11]([CH3:14])([CH3:13])[N:10]([Si:15]([CH3:18])([CH3:17])[CH3:16])[C:2]1[CH:3]=[C:4]([Si:28]([CH3:35])([CH3:34])[O:29][Si:30]([C:7]2[CH:21]=[CH:20][CH:19]=[C:9]([N:10]([Si:15]([CH3:18])([CH3:17])[CH3:16])[Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=2)([CH3:32])[CH3:31])[CH:25]=[CH:26][CH:1]=1

Participants

Conditions

Temperature: 0 °C

Procedure

There was added 2.6 moles of butyl lithium in hexane over a 15 minute period to a mixture of 50 grams of the 3-bromo-N,N-bis(trimethylsilyl)aniline in 400 ml. of anhydrous ether cooled to 0° C. under a nitrogen atmosphere. The resulting reaction mixture was allowed to stir for an additional 2 hours at 0° C. The mixture was then added to a mixture of 100 ml. of anhydrous ether and 16.06 grams of 1,3-dichloro-1,1,3,3-tetramethyldisiloxane at 0° C. After the solution was filtered and the solvents were removed under reduced pressure, there was obtained a 77% yield of 1,3-bis[N,N-bis(trimethylsilyl)-3-aminophenyl]-1,1,3,3-tetramethyldisiloxane in the form of a pale-yellow oil having a boiling point of about 169°-174° C.

Workup

customThe resulting reaction mixture
additionThe mixture was then added to a mixture of 100 ml
customat 0° C
filtrationAfter the solution was filtered
customthe solvents were removed under reduced pressure

Sources & evidence

ORD record: ord-462391df55ba4bdd924d633f561e3625
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04690997

Reaction notes

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