(E)-1-(3-Chloromethyl-4-hydroxy-2,3-dihydro-benzo[f]indol-1-yl)-3-(3-methoxy-phenyl)-propenone

Base Information

Chemical Name:(E)-1-(3-Chloromethyl-4-hydroxy-2,3-dihydro-benzo[f]indol-1-yl)-3-(3-methoxy-phenyl)-propenone
CAS No.:198709-13-6
Molecular Formula:C₂₃H₂₀ClNO₃
Molecular Weight:393.87
Hs Code.:

Synonyms:(E)-1-(3-Chloromethyl-4-hydroxy-2,3-dihydro-benzo[f]indol-1-yl)-3-(3-methoxy-phenyl)-propenone

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Chemical Property of (E)-1-(3-Chloromethyl-4-hydroxy-2,3-dihydro-benzo[f]indol-1-yl)-3-(3-methoxy-phenyl)-propenone

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Technology Process of (E)-1-(3-Chloromethyl-4-hydroxy-2,3-dihydro-benzo[f]indol-1-yl)-3-(3-methoxy-phenyl)-propenone

There total 10 articles about (E)-1-(3-Chloromethyl-4-hydroxy-2,3-dihydro-benzo[f]indol-1-yl)-3-(3-methoxy-phenyl)-propenone 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:

: 6099-04-3,17570-26-2
trans-3-methoxycinnamic acid

: 3-Chloromethyl-2,3-dihydro-1H-benzo[f]indol-4-ol; hydrochloride

: 198709-13-6
(E)-1-(3-Chloromethyl-4-hydroxy-2,3-dihydro-benzo[f]indol-1-yl)-3-(3-methoxy-phenyl)-propenone

Guidance literature:: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25 ℃; for 3h; Yield given;
DOI:10.1021/jo971686p

Reference yield:

: 139975-98-7
tert-butyl-(4-hydroxynaphthalen-2-yl)carbamate

: 198709-13-6
(E)-1-(3-Chloromethyl-4-hydroxy-2,3-dihydro-benzo[f]indol-1-yl)-3-(3-methoxy-phenyl)-propenone

Guidance literature:: Multi-step reaction with 8 steps

1: 78 percent / Bu₄NI, NaH / dimethylformamide / 5 h / 25 °C

2: 1.) n-BuLi, TMEDA, 2.) ICH₂CH₂Cl / 1.) THF, hexane, -25 deg C, 2 h. 2.) THF, hexane, 25 deg C, 15 min

3: 94 percent / NaH / dimethylformamide / 1 h / 25 °C

4: 94 percent / Bu₃SnH / benzene / 1.5 h / 50 °C

5: 87 percent / Zn / acetic acid; H₂O; tetrahydrofuran / 1 h / 70 °C

6: 90 percent / CCl₄, PPh₃ / CH₂Cl₂ / 2 h / 25 °C

7: HCl / ethyl acetate / 0.5 h / 25 °C

8: EDCI / dimethylformamide / 3 h / 25 °C

With hydrogenchloride; tetrachloromethane; n-butyllithium; 1-chloro-2-iodoethane; N,N,N,N,-tetramethylethylenediamine; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; zinc; In tetrahydrofuran; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo971686p

Reference yield:

: 198708-95-1
N-(tert-Butyloxycarbonyl)-4-(methoxymethoxy)-2-naphthylamine

: 198709-13-6
(E)-1-(3-Chloromethyl-4-hydroxy-2,3-dihydro-benzo[f]indol-1-yl)-3-(3-methoxy-phenyl)-propenone

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) n-BuLi, TMEDA, 2.) ICH₂CH₂Cl / 1.) THF, hexane, -25 deg C, 2 h. 2.) THF, hexane, 25 deg C, 15 min

2: 94 percent / NaH / dimethylformamide / 1 h / 25 °C

3: 94 percent / Bu₃SnH / benzene / 1.5 h / 50 °C

4: 87 percent / Zn / acetic acid; H₂O; tetrahydrofuran / 1 h / 70 °C

5: 90 percent / CCl₄, PPh₃ / CH₂Cl₂ / 2 h / 25 °C

6: HCl / ethyl acetate / 0.5 h / 25 °C

7: EDCI / dimethylformamide / 3 h / 25 °C

With hydrogenchloride; tetrachloromethane; n-butyllithium; 1-chloro-2-iodoethane; N,N,N,N,-tetramethylethylenediamine; tri-n-butyl-tin hydride; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; zinc; In tetrahydrofuran; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo971686p