(Z)-3-(((tert-butyldimethylsilyl)oxy)methylene)-5,5-dimethyl-4-methylene-1-tosyl-1,3,4,5-tetrahydrobenzo[cd]indole

Base Information

Chemical Name:(Z)-3-(((tert-butyldimethylsilyl)oxy)methylene)-5,5-dimethyl-4-methylene-1-tosyl-1,3,4,5-tetrahydrobenzo[cd]indole
CAS No.:1335030-90-4
Molecular Formula:C₂₈H₃₅NO₃SSi
Molecular Weight:493.742
Hs Code.:

Synonyms:(Z)-3-(((tert-butyldimethylsilyl)oxy)methylene)-5,5-dimethyl-4-methylene-1-tosyl-1,3,4,5-tetrahydrobenzo[cd]indole

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Chemical Property of (Z)-3-(((tert-butyldimethylsilyl)oxy)methylene)-5,5-dimethyl-4-methylene-1-tosyl-1,3,4,5-tetrahydrobenzo[cd]indole

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Technology Process of (Z)-3-(((tert-butyldimethylsilyl)oxy)methylene)-5,5-dimethyl-4-methylene-1-tosyl-1,3,4,5-tetrahydrobenzo[cd]indole

There total 6 articles about (Z)-3-(((tert-butyldimethylsilyl)oxy)methylene)-5,5-dimethyl-4-methylene-1-tosyl-1,3,4,5-tetrahydrobenzo[cd]indole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

: 1335030-88-0
4,5,5-trimethyl-1-tosyl-1,5-dihydrobenzo[cd]indole-3-carbaldehyde

: 69739-34-0
t-butyldimethylsiyl triflate

: 1335030-90-4
(Z)-3-(((tert-butyldimethylsilyl)oxy)methylene)-5,5-dimethyl-4-methylene-1-tosyl-1,3,4,5-tetrahydrobenzo[cd]indole

Guidance literature:: With triethylamine; In dichloromethane; at -10 ℃; for 10h; Inert atmosphere;
DOI:10.1002/anie.201100957

Reference yield:

: 1335030-84-6
4,5,5-trimethyl-4,5-dihydrobenzo[cd]indol-3(1H)-one

: 1335030-90-4
(Z)-3-(((tert-butyldimethylsilyl)oxy)methylene)-5,5-dimethyl-4-methylene-1-tosyl-1,3,4,5-tetrahydrobenzo[cd]indole

Guidance literature:: Multi-step reaction with 5 steps

1.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 15.5 h / 0 - 20 °C / Inert atmosphere

2.1: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 22 h / 0 - 20 °C / Inert atmosphere

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / toluene / 1 h / 0 °C / Inert atmosphere

4.2: 6 h / 0 - 20 °C / Inert atmosphere

5.1: triethylamine / dichloromethane / 10 h / -10 °C / Inert atmosphere

With dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,6-di-tert-butyl-4-methylpyridine; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/anie.201100957

Reference yield:

: 1335031-03-2
4,5,5-trimethyl-1-tosyl-1,5-dihydrobenzo[cd]indol-3-yl trifluoromethanesulfonate

: 1335030-90-4
(Z)-3-(((tert-butyldimethylsilyl)oxy)methylene)-5,5-dimethyl-4-methylene-1-tosyl-1,3,4,5-tetrahydrobenzo[cd]indole

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / toluene / 1 h / 0 °C / Inert atmosphere

2.2: 6 h / 0 - 20 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 10 h / -10 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisobutylaluminium hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/anie.201100957