Water → HCID 15501724, 화합물

HRID 369506노트

반응식

HRID 369506 반응식
C([Li])CCC.[CH3:6][CH:7]([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].S(C1C=CC(C)=CC=1)(O[CH2:24][CH2:25][N:26]([CH3:28])[CH3:27])(=O)=O.O>C1COCC1>[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:7]([CH3:6])[CH3:8])[CH3:28]

참가 물질

6

반응물 4

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

생성물 1

HCID 15501724HCID 15501724, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

In a dry 500 mL three-necked flask with a magnetic stirrer, a solution of 62.5 mL of n-butyllithium (1.6M in n-hexane; 100 mmol) was added under a dry nitrogen atmosphere to a solution of 19.2 g (100 mmol) of tri-(2-propyl)cyclopentadiene in 250 mL of THF at -60° C. After heating to room temperature (in approximately 1 hour) stirring continued for a further 2 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. The degree of conversion of the reaction was monitored by GC. After addition of water, the product was extracted with petroleum ether (40-60° C.). The combined organic layer was dried (Na2SO4) and evaporated under reduced pressure. The conversion was greater than 95%. 30% of the product is geminally substituted.

후처리

  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 (Na2SO4)
  8. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-499d06a2bfcf4f5eabe6c4252d029413
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06137019

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