반응 #358981

반응 방정식

n-BuLi

9-(4-tert-butylphenyl)-2-methyl-5,6,7,8-tetrahydro-1H-cyclopenta[b]naphthalene

9-(4-tert-Butylphenyl)-2-methyl-5,6,7,8-tetrahydro-1H-cyclopenta[b]naphthalene

chloro-(4-(4-tert-butylphenyl)-2-isopropyl-1H-inden-1-yl)-dimethylsilane

CuCN

→

[4-(4-t-butylphenyl)-2-isopropyl-1H-inden-1-yl][4-(4-tert-butylphenyl)-2-methyl-5,6,7,8-tetrahydro-1H-cyclopenta[b]naphthalen-1-yl]dimethylsilane

용매

hexane

Water

Et2O

Et2O

반응 조건

후처리

1. 1
   온도cooled to −60° C.
2. 2
   workup.WAITAfter 15 min
3. 3
   기타resulting mixture
4. 4
   온도to warm to room temperature
5. 5
   workup.STIRRINGstirred for 16 h
6. 6
   기타organic phase was separated
7. 7
   건조dried over MgSO4
8. 8
   기타evaporated
9. 9
   기타The product was dried in vacuo
10. 10
    기타used without purification

실험 절차

Solution of 9-(4-tert-butylphenyl)-2-methyl-5,6,7,8-tetrahydro-1H-cyclopenta[b]naphthalene (4d, 2.97 g, 9.38 mmol) in Et2O (50 ml) was cooled to −60° C., and n-BuLi (1.6 M in hexane, 6.04 ml, 9.67 mmol) was added. The resulting mixture was allowed to warm to room temperature, stirred for 3 h, cooled to −60° C., and CuCN (50 mg, 0.55 mmol) was added. After 15 min, solution of chloro-(4-(4-tert-butylphenyl)-2-isopropyl-1H-inden-1-yl)-dimethylsilane (9.67 mmol) in Et2O (24 ml) was added, and resulting mixture was allowed to warm to room temperature and stirred for 16 h. Water (5 ml) and hexane (200 ml) were added, organic phase was separated, dried over MgSO4, passed through silica gel and evaporated. The product was dried in vacuo and used without purification.

출처