(3E,10E)-8-Benzyloxymethyl-9-[1-methoxy-meth-(Z)-ylidene]-trideca-3,10-dien-5-one

Base Information

Chemical Name:(3E,10E)-8-Benzyloxymethyl-9-[1-methoxy-meth-(Z)-ylidene]-trideca-3,10-dien-5-one
CAS No.:192126-19-5
Molecular Formula:C₂₃H₃₂O₃
Molecular Weight:356.505
Hs Code.:

Synonyms:(3E,10E)-8-Benzyloxymethyl-9-[1-methoxy-meth-(Z)-ylidene]-trideca-3,10-dien-5-one

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Chemical Property of (3E,10E)-8-Benzyloxymethyl-9-[1-methoxy-meth-(Z)-ylidene]-trideca-3,10-dien-5-one

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Technology Process of (3E,10E)-8-Benzyloxymethyl-9-[1-methoxy-meth-(Z)-ylidene]-trideca-3,10-dien-5-one

There total 11 articles about (3E,10E)-8-Benzyloxymethyl-9-[1-methoxy-meth-(Z)-ylidene]-trideca-3,10-dien-5-one 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:

: 192126-33-3
(E)-5-Benzyloxymethyl-2-((E)-but-1-enyl)-6-[1-methoxy-meth-(Z)-ylidene]-2-trimethylsilanyloxy-dec-7-enenitrile

: 192126-19-5
(3E,10E)-8-Benzyloxymethyl-9-[1-methoxy-meth-(Z)-ylidene]-trideca-3,10-dien-5-one

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.0833333h; Yield given;
DOI:10.1002/anie.199711941

Reference yield:

: 192126-21-9
2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-pent-4-enal

: 192126-19-5
(3E,10E)-8-Benzyloxymethyl-9-[1-methoxy-meth-(Z)-ylidene]-trideca-3,10-dien-5-one

Guidance literature:: Multi-step reaction with 11 steps

1: NaBH₄ / methanol / 0.17 h / 22 °C

2: 88 percent / NaH, (n-Bu)4NI / dimethylformamide / 15 h / 0 °C

3: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) -78 to 22 deg C, 15 h

4: 98 percent / 4 Angstroem molecular sieves / benzene / 15 h / 22 °C

5: LDA / tetrahydrofuran / 1.) -5 deg C, 0.5 h, 2.) -78 to 22 deg C, 4 h

6: 6percent aq. oxalic acid / 0.5 h / 22 °C

7: 96 percent / KH / 1,2-dimethoxy-ethane; hexamethylphosphoric acid triamide / 1.) 0 deg C, 0.5 h, 2.) 0 deg C, 0.5 h

8: 96 percent / aq. TBAF / tetrahydrofuran / 3 h / 22 °C

9: 78 percent / I₂, Ph₃P, imidazole / CH₂Cl₂ / 0.08 h / 22 °C

10: LiHMDS / tetrahydrofuran / 0.5 h / 0 °C

11: aq. TBAF / tetrahydrofuran / 0.08 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; 4 A molecular sieve; tetrabutyl ammonium fluoride; iodine; oxalic acid; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; ozone; triphenylphosphine; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1002/anie.199711941

Reference yield:

: 192126-22-0
2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-pent-4-en-1-ol

: 192126-19-5
(3E,10E)-8-Benzyloxymethyl-9-[1-methoxy-meth-(Z)-ylidene]-trideca-3,10-dien-5-one

Guidance literature:: Multi-step reaction with 10 steps

1: 88 percent / NaH, (n-Bu)4NI / dimethylformamide / 15 h / 0 °C

2: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) -78 to 22 deg C, 15 h

3: 98 percent / 4 Angstroem molecular sieves / benzene / 15 h / 22 °C

4: LDA / tetrahydrofuran / 1.) -5 deg C, 0.5 h, 2.) -78 to 22 deg C, 4 h

5: 6percent aq. oxalic acid / 0.5 h / 22 °C

6: 96 percent / KH / 1,2-dimethoxy-ethane; hexamethylphosphoric acid triamide / 1.) 0 deg C, 0.5 h, 2.) 0 deg C, 0.5 h

7: 96 percent / aq. TBAF / tetrahydrofuran / 3 h / 22 °C

8: 78 percent / I₂, Ph₃P, imidazole / CH₂Cl₂ / 0.08 h / 22 °C

9: LiHMDS / tetrahydrofuran / 0.5 h / 0 °C

10: aq. TBAF / tetrahydrofuran / 0.08 h / 0 °C

With 1H-imidazole; 4 A molecular sieve; tetrabutyl ammonium fluoride; iodine; oxalic acid; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; ozone; triphenylphosphine; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1002/anie.199711941