(E)-6-(4-Methoxy-benzyloxy)-tridec-3-ene-2,10-dione

Base Information

Chemical Name:(E)-6-(4-Methoxy-benzyloxy)-tridec-3-ene-2,10-dione
CAS No.:339563-80-3
Molecular Formula:C₂₁H₃₀O₄
Molecular Weight:346.467
Hs Code.:

Synonyms:(E)-6-(4-Methoxy-benzyloxy)-tridec-3-ene-2,10-dione

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Chemical Property of (E)-6-(4-Methoxy-benzyloxy)-tridec-3-ene-2,10-dione

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Technology Process of (E)-6-(4-Methoxy-benzyloxy)-tridec-3-ene-2,10-dione

There total 12 articles about (E)-6-(4-Methoxy-benzyloxy)-tridec-3-ene-2,10-dione 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:

: 87184-80-3
5-tert-butyldimethylsilyloxypentanal

: 339563-80-3
(E)-6-(4-Methoxy-benzyloxy)-tridec-3-ene-2,10-dione

Guidance literature:: Multi-step reaction with 11 steps

1.1: 51 percent / Zn / dimethylformamide / 2 h / 20 °C / sonication

2.1: 70 percent / Et₃N; DMAP / CH₂Cl₂ / 24 h / 20 °C

3.1: 77 percent / HF*pyr / tetrahydrofuran / 4 h

4.1: H₂ / Pd/C / ethyl acetate / 1 h / 760.05 Torr

5.1: 423 mg / (COCl)2; DMSO; Et₃N / CH₂Cl₂

6.1: diisopropylamine; n-BuLi / tetrahydrofuran; various solvent(s) / 0.5 h / -78 °C

6.2: 88 percent / tetrahydrofuran; various solvent(s) / 30 h / -78 °C

7.1: 86 percent / BF₃*OEt₂ / CH₂Cl₂ / 4 h / 0 °C

8.1: 87 percent / DIBAL / toluene / 0.67 h / -78 °C

9.1: 82 percent / DIPEA; LiCl / acetonitrile / 3 h

10.1: 90 percent / CSA / methanol / 3 h / 20 °C

11.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.67 h

With dmap; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 5.1: Swern oxidation / 11.1: Dess-Martin oxidation;
DOI:10.5555/ol015556l

Reference yield:

: 339563-66-5
8-(tert-butyl-dimethyl-silanyloxy)-oct-1-en-4-ol

: 339563-80-3
(E)-6-(4-Methoxy-benzyloxy)-tridec-3-ene-2,10-dione

Guidance literature:: Multi-step reaction with 10 steps

1.1: 70 percent / Et₃N; DMAP / CH₂Cl₂ / 24 h / 20 °C

2.1: 77 percent / HF*pyr / tetrahydrofuran / 4 h

3.1: H₂ / Pd/C / ethyl acetate / 1 h / 760.05 Torr

4.1: 423 mg / (COCl)2; DMSO; Et₃N / CH₂Cl₂

5.1: diisopropylamine; n-BuLi / tetrahydrofuran; various solvent(s) / 0.5 h / -78 °C

5.2: 88 percent / tetrahydrofuran; various solvent(s) / 30 h / -78 °C

6.1: 86 percent / BF₃*OEt₂ / CH₂Cl₂ / 4 h / 0 °C

7.1: 87 percent / DIBAL / toluene / 0.67 h / -78 °C

8.1: 82 percent / DIPEA; LiCl / acetonitrile / 3 h

9.1: 90 percent / CSA / methanol / 3 h / 20 °C

10.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.67 h

With dmap; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; acetonitrile; 4.1: Swern oxidation / 10.1: Dess-Martin oxidation;
DOI:10.5555/ol015556l

Reference yield:

: 339563-50-7
5-(tert-butyl-dimethyl-silanyloxy)-oct-7-en-1-ol

: 339563-80-3
(E)-6-(4-Methoxy-benzyloxy)-tridec-3-ene-2,10-dione

Guidance literature:: Multi-step reaction with 8 steps

1.1: H₂ / Pd/C / ethyl acetate / 1 h / 760.05 Torr

2.1: 423 mg / (COCl)2; DMSO; Et₃N / CH₂Cl₂

3.1: diisopropylamine; n-BuLi / tetrahydrofuran; various solvent(s) / 0.5 h / -78 °C

3.2: 88 percent / tetrahydrofuran; various solvent(s) / 30 h / -78 °C

4.1: 86 percent / BF₃*OEt₂ / CH₂Cl₂ / 4 h / 0 °C

5.1: 87 percent / DIBAL / toluene / 0.67 h / -78 °C

6.1: 82 percent / DIPEA; LiCl / acetonitrile / 3 h

7.1: 90 percent / CSA / methanol / 3 h / 20 °C

8.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.67 h

With n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; acetonitrile; 2.1: Swern oxidation / 8.1: Dess-Martin oxidation;
DOI:10.5555/ol015556l