Water → HCID 15501724, compound

HRID 1421133Notes

Reaction equation

HRID 1421133 reaction equation
C([Li])CCC.[CH:6]([C:9]1[C:10]([CH:17]([CH3:19])[CH3:18])=[C:11]([CH:14]([CH3:16])[CH3:15])[CH2:12][CH:13]=1)([CH3:8])[CH3:7].S(C1C=CC(C)=CC=1)(O[CH2:24][CH2:25][N:26]([CH3:28])[CH3:27])(=O)=O.O>O1CCCC1>[CH3:27][N:26]([CH2:25][CH2:24][C:13]1[CH2:12][C:11]([CH:14]([CH3:16])[CH3:15])=[C:10]([CH:17]([CH3:19])[CH3:18])[C:9]=1[CH:6]([CH3:8])[CH3:7])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 109557742-(dimethylamino)ethyl 4-methylbenzenesulfonateHCID 156679961,2,3-Tri(propan-2-yl)cyclopenta-1,3-dieneHCID 178418339Butyllithium

Product 1

HCID 15501724HCID 15501724, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a dry 500 mL three-necked flask with a magnetic stirrer, a solution of 62.5 mL of n-butyllithium (1.6 M in n-hexane; 100 mmol) was added under a dry nitrogen atmosphere to a solution of 19.2 g (100 mmol) of triisopropyl-cyclopentadiene in 250 mL of tetrahydrofuran at -60° C. After heating to room temperature (in approximately one hour) stirring continued for a further two hours. After cooling to -60° C., a solution of dimethylaminoethyl tosylate (105 mmol) prepared in situ was added over a period of 5 minutes. The reaction mixture was heated to room temperature, followed by overnight stirring. After addition of water, the product was extracted with petroleum ether (40-60° C.). The combined organic layer was dried with sodium sulphate, and evaporated under reduced pressure. The conversion was greater than 95%. The yield of product after distillation (based on triisopropyl-cyclopentadiene) was approximately 55%.

Workup

  1. temperatureAfter cooling to -60° C.
  2. additionwas added over a period of 5 minutes
  3. temperatureThe reaction mixture was heated to room temperature
  4. waitfollowed by overnight
  5. stirringstirring
  6. extractionthe product was extracted with petroleum ether (40-60° C.)
  7. dry with materialThe combined organic layer was dried with sodium sulphate
  8. customevaporated under reduced pressure
  9. distillationThe yield of product after distillation (based on triisopropyl-cyclopentadiene)

Sources & evidence

ORD record
ord-4a8ca3f0c20040b2a98b06dd8726735d
Source dataset
uspto-grants-2000_06
Patent number
US06072067

Reaction notes

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