Hexane → HCID 131721845, 화합물

HRID 1421131노트

반응식

HRID 1421131 반응식
C([Li])CCC.CCCCCC.[CH:12]1([C:18]2([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:22]=[CH:21][CH:20]=[CH:19]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.S(C1C=CC(C)=CC=1)(O[CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])(=O)=O>O1CCCC1.O>[CH3:36][N:35]([CH2:34][CH2:33][C:19]1[C:18]([CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)([CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[CH:22]=[CH:21][CH:20]=1)[CH3:37]

참가 물질

7

반응물 4

HCID 8058HexaneHCID 109557742-(dimethylamino)ethyl 4-methylbenzenesulfonateHCID 131721844HCID 131721844, 화합물HCID 178418339Butyllithium

생성물 1

HCID 131721845HCID 131721845, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Under a nitrogen atmosphere, a solution of n-butyllithium in hexane (18.7 mL; 1.6 mol/L; 30 mmol) was added dropwise to a cooled (0° C.) solution of dicyclohexyl-cyclopentadiene (Example IV) (6.90 g; 30.0 mmol) in dry tetrahydrofuran (125 ml) in a 250 mL three-necked round-bottomed flask provided with a magnetic stirrer and a dropping funnel. After 24 hours of stirring at room temperature, 30.0 mmol of 2-dimethylaminoethyl tosylate prepared in situ were added. After 18 hours of stirring, the conversion was found to be 88%, and water (100 ml) was carefully added dropwise to the reaction mixture and the tetrahydrofuran was then distilled off. The crude product was extracted with ether, and the combined organic phase was then dried with sodium sulphate, and evaporated to dryness. The residue was purified on a silica gel column, which resulted in 7.4 g of (dimethylaminoethyl)dicyclohexylcyclo-pentadiene.

후처리

  1. customprovided with a magnetic stirrer and a dropping funnel
  2. additionwere added
  3. stirringAfter 18 hours of stirring
  4. additionwas carefully added dropwise to the reaction mixture
  5. distillationthe tetrahydrofuran was then distilled off
  6. extractionThe crude product was extracted with ether
  7. dry with materialthe combined organic phase was then dried with sodium sulphate
  8. customevaporated to dryness
  9. customThe residue was purified on a silica gel column, which
  10. customresulted in 7.4 g of (dimethylaminoethyl)dicyclohexylcyclo-pentadiene

출처 및 근거

ORD 기록
ord-09258765b5214fdba944e3d7e8044ee1
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06072067

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