4-Toluenesulfonyl chloride → HCID 131721810, compound

HRID 1955397Notes

Reaction equation

[CH:1]1([C:7]2[C:11]([CH:15]([CH3:17])[CH3:16])([CH:12]([CH3:14])[CH3:13])[CH:10]=[CH:9][CH:8]=2)CCCC[CH2:2]1.C([Li])CCC.[CH3:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[CH3:29][N:30](CCO)[CH3:31].S(Cl)(C1C=CC(C)=CC=1)(=O)=O>C1COCC1>[CH:25]1([C:8]2[CH:9]=[CH:10][C:11]([CH:15]([CH3:17])[CH3:16])([CH:12]([CH3:14])[CH3:13])[C:7]=2[CH2:1][CH2:2][N:30]([CH3:31])[CH3:29])[CH2:24][CH2:23][CH2:28][CH2:27][CH2:26]1

Participants

Conditions

Temperature: -78 °C

Procedure

In a Schlenk vessel, to a solution of cyclohexyldiisopropylcyclopentadiene (9.28 g; 40.0 mmol) in dry THF (150 mL) at room temperature, a solution of n-butyllithium in hexane (25.0 mL; 1.6 mol/L; 40.0 mmol) was added dropwise. Then, in another Schlenk vessel, a solution of n-butyllithium in hexane (25.0 mL; 1.6 mol/L; 40.0 mmol) was added dropwise to a cold (-78° C.) solution of dimethylaminoethanol (3.56 g; 40.0 mmol) in THF (100 mL). After an hour and a half's stirring at room temperature, the mixture was again cooled to -78° C. and the solid tosyl chloride (8.10 g; 40.0 mmol) was added slowly. The mixture was brought to 0° C., being stirred for 5 minutes in the process, again cooled to -78° C., and the mixture from the first Schlenk vessel then added at once. After 16 hours' stirring at room temperature the conversion was 100%. After column chromatography 11.1 g of cyclohexyl(dimethylaminoethyl)-di-(2-propyl)cyclopentadiene were obtained.

Workup

waitAfter an hour
customwas brought to 0° C.
temperatureagain cooled to -78° C.
additionthe mixture from the first Schlenk vessel then added at once
stirringAfter 16 hours' stirring at room temperature the conversion

Sources & evidence

ORD record: ord-4c21f3b8d064496e9163477429e7be79
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06124488

Reaction notes

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