Acetic acid 11-[(E)-benzyloxyimino]-4,9-dimethoxy-5,10-dioxo-10,11-dihydro-5H-benzo[b]fluoren-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid 11-[(E)-benzyloxyimino]-4,9-dimethoxy-5,10-dioxo-10,11-dihydro-5H-benzo[b]fluoren-2-ylmethyl ester
• CAS No.: 202195-15-1
• Molecular Formula: C₂₉H₂₃NO₇
• Molecular Weight: 497.504
• Mol file: 202195-15-1.mol

Synonyms:

Chemical Property of Acetic acid 11-[(E)-benzyloxyimino]-4,9-dimethoxy-5,10-dioxo-10,11-dihydro-5H-benzo[b]fluoren-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid 11-[(E)-benzyloxyimino]-4,9-dimethoxy-5,10-dioxo-10,11-dihydro-5H-benzo[b]fluoren-2-ylmethyl ester

There total 10 articles about Acetic acid 11-[(E)-benzyloxyimino]-4,9-dimethoxy-5,10-dioxo-10,11-dihydro-5H-benzo[b]fluoren-2-ylmethyl ester 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: 53.0%

Acetic acid 11-[(E)-benzyloxyimino]-4,5,9,10-tetramethoxy-11H-benzo[b]fluoren-2-ylmethyl ester (202195-14-0) → Acetic acid 11-[(E)-benzyloxyimino]-4,9-dimethoxy-5,10-dioxo-10,11-dihydro-5H-benzo[b]fluoren-2-ylmethyl ester (202195-15-1)

Guidance literature:

With Pyridine-2,6-dicarboxylic acid N-oxide; ammonium cerium(IV) nitrate; In acetonitrile; 1.) 0 deg C, 20 min, 2.) r.t., 1 h;

Reference yield:

3-methoxy-5-methyl-benzaldehyde (90674-26-3) → Acetic acid 11-[(E)-benzyloxyimino]-4,9-dimethoxy-5,10-dioxo-10,11-dihydro-5H-benzo[b]fluoren-2-ylmethyl ester (202195-15-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 69 percent / N,N,N'-trimethylethylenediamine, n-BuLi, BrCF₂CF₂Br / tetrahydrofuran; hexane / 1.) -65 deg C, 30 min; -20 deg C, 14 h, 2.) -60 deg C

3: 91 percent / 35percent H₂O₂, 15percent aq. NaOH / methanol / 1 h / 90 °C

4: (COCl)2, DMF / CH₂Cl₂ / 1.5 h

5: TiCl₄ / CH₂Cl₂ / 2 h / 0 °C

6: NBS, (PhCO₂)2 / CCl₄ / 48 h / Heating

7: CaCO₃ / dioxane; H₂O / 20 h / Heating

8: 94 percent / DMAP, pyridine / 0.03 h

9: 95 percent / aq. AcONa / methanol / Heating

10: 53 percent / aq. (NH₄)2Ce(NO₃)6, pyridine-2,6-dicarboxylic acid N-oxide / acetonitrile / 1.) 0 deg C, 20 min, 2.) r.t., 1 h

With pyridine; Pyridine-2,6-dicarboxylic acid N-oxide; dmap; sodium hydroxide; N-Bromosuccinimide; n-butyllithium; oxalyl dichloride; ammonium cerium(IV) nitrate; 1,2-dibromo-1,1,2,2-tetrafluoroethane; dihydrogen peroxide; sodium acetate; titanium tetrachloride; N,N',N'-trimethylenediamine; N,N-dimethyl-formamide; calcium carbonate; dibenzoyl peroxide; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; hexane; dichloromethane; water; acetonitrile;

Reference yield:

2-bromo-3-methoxy-5-methylbenzaldehyde (202195-05-9) → Acetic acid 11-[(E)-benzyloxyimino]-4,9-dimethoxy-5,10-dioxo-10,11-dihydro-5H-benzo[b]fluoren-2-ylmethyl ester (202195-15-1)

Guidance literature:

Multi-step reaction with 9 steps

2: 91 percent / 35percent H₂O₂, 15percent aq. NaOH / methanol / 1 h / 90 °C

3: (COCl)2, DMF / CH₂Cl₂ / 1.5 h

4: TiCl₄ / CH₂Cl₂ / 2 h / 0 °C

5: NBS, (PhCO₂)2 / CCl₄ / 48 h / Heating

6: CaCO₃ / dioxane; H₂O / 20 h / Heating

7: 94 percent / DMAP, pyridine / 0.03 h

8: 95 percent / aq. AcONa / methanol / Heating

9: 53 percent / aq. (NH₄)2Ce(NO₃)6, pyridine-2,6-dicarboxylic acid N-oxide / acetonitrile / 1.) 0 deg C, 20 min, 2.) r.t., 1 h

With pyridine; Pyridine-2,6-dicarboxylic acid N-oxide; dmap; sodium hydroxide; N-Bromosuccinimide; oxalyl dichloride; ammonium cerium(IV) nitrate; dihydrogen peroxide; sodium acetate; titanium tetrachloride; N,N-dimethyl-formamide; calcium carbonate; dibenzoyl peroxide; In 1,4-dioxane; methanol; tetrachloromethane; dichloromethane; water; acetonitrile;

upstream raw materials:

Acetic acid 11-[(E)-benzyloxyimino]-4,5,9,10-tetramethoxy-11H-benzo[b]fluoren-2-ylmethyl ester

3-methoxy-5-methyl-benzaldehyde

tri-O-methylkinafluorenone

2-bromo-3-methoxy-5-methylbenzaldehyde