Diisopropylamine → 1-(3-Fluorophenyl)-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane

HRID 1637822Notes

Reaction equation

C(NC(C)C)(C)C.[F:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12].[CH3:16][Si:17](Cl)([CH2:19][CH2:20][Si:21](Cl)([CH3:23])[CH3:22])[CH3:18]>O1CCCC1>[F:8][C:9]1[CH:10]=[C:11]([N:12]2[Si:21]([CH3:23])([CH3:22])[CH2:20][CH2:19][Si:17]2([CH3:18])[CH3:16])[CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of freshly distilled diisopropylamine (22.9 mL) in dry tetrahydrofuran (175 mL) at -78° C. under N2 is treated with n-butylithium (1.6 M in hexanes, 109 mL) dropwise over 15 minutes, and the resulting mixture is stirred at -78° C. for 45 minutes and is then added over ten minutes via cannula to a solution of 3-fluoroaniline (8.00 mL) in dry tetrahydrofuran (166 mL) at -78° C. under N2. The resulting reaction mixture is stirred at -78° C. for 50 minutes and is then treated with a solution of 1,1,4,4-tetramethyl-1,4-dichlorodisilethylene (18.3 g) in dry tetrahydrofuran (85 mL). The mixture is allowed to slowly warm to ambient temperature over four hours with stirring and is then washed with water (2×200 mL) and saline (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound, NMR (CDCl3, 400 MHz) 7.12, 6.65, 6.58, 0.86, 0.24 δ.

Workup

customThe resulting reaction mixture
stirringis stirred at -78° C. for 50 minutes
temperatureto slowly warm to ambient temperature over four hours
stirringwith stirring
washis then washed with water (2×200 mL) and saline (100 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-ca9d411603ba4deaa674dee092460c85
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06043266

Reaction notes

Loading…