(1E,4S)-1-(2-bromo-3,4,5-trimethoxyphenyl)-1-hepten-4-ol

Base Information

• Chemical Name: (1E,4S)-1-(2-bromo-3,4,5-trimethoxyphenyl)-1-hepten-4-ol
• CAS No.: 123808-05-9
• Molecular Formula: C₁₆H₂₃BrO₄
• Molecular Weight: 359.26
• Mol file: 123808-05-9.mol

Synonyms:

Chemical Property of (1E,4S)-1-(2-bromo-3,4,5-trimethoxyphenyl)-1-hepten-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1E,4S)-1-(2-bromo-3,4,5-trimethoxyphenyl)-1-hepten-4-ol

There total 17 articles about (1E,4S)-1-(2-bromo-3,4,5-trimethoxyphenyl)-1-hepten-4-ol 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:

(S)-(-)-1,2-pentanediol (29117-54-2) → (1E,4S)-1-(2-bromo-3,4,5-trimethoxyphenyl)-1-hepten-4-ol (123808-05-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) HBr; 2.) 50percent aq. KOH / 1.) AcOH, 1h; 2.) 120 deg C

2: aq. ethanol / 19 h / Heating

4: 83 percent / imidazole / dimethylformamide / 15 h / Ambient temperature

5: 95 percent / lithium borohydride, lithium triethylborohydride / diethyl ether; tetrahydrofuran / 3 h / Heating

6: pyridine / 3 h / 0 - 5 °C

7: 88 percent / NaI, NaHCO₃ / acetone / 2 h / Heating

8: 86 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

9: sodium acetate, bromine / 2 h / Ambient temperature

10: NaOH / methanol / 1 h / Ambient temperature

11: triethylamine / tetrahydrofuran / 2 h / 0 °C

12: DBU / benzene / 2 h / Heating

13: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature

With 1H-imidazole; potassium hydroxide; sodium hydroxide; lithium borohydride; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen bromide; bromine; sodium acetate; lithium triethylborohydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; hexane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/S0040-4020(01)80027-2

Reference yield:

2-(S)-hydroxyvaleric acid (41014-93-1,6450-97-1) → (1E,4S)-1-(2-bromo-3,4,5-trimethoxyphenyl)-1-hepten-4-ol (123808-05-9)

Guidance literature:

Multi-step reaction with 14 steps

1: 66 percent / LAH / diethyl ether / 1.) 0 deg C, then 3 h rt.

2: 1.) HBr; 2.) 50percent aq. KOH / 1.) AcOH, 1h; 2.) 120 deg C

3: aq. ethanol / 19 h / Heating

5: 83 percent / imidazole / dimethylformamide / 15 h / Ambient temperature

6: 95 percent / lithium borohydride, lithium triethylborohydride / diethyl ether; tetrahydrofuran / 3 h / Heating

7: pyridine / 3 h / 0 - 5 °C

8: 88 percent / NaI, NaHCO₃ / acetone / 2 h / Heating

9: 86 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

10: sodium acetate, bromine / 2 h / Ambient temperature

11: NaOH / methanol / 1 h / Ambient temperature

12: triethylamine / tetrahydrofuran / 2 h / 0 °C

13: DBU / benzene / 2 h / Heating

14: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature

With 1H-imidazole; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen bromide; bromine; sodium acetate; lithium triethylborohydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; hexane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/S0040-4020(01)80027-2

Reference yield:

L-Norvaline (6600-40-4,498-18-0) → (1E,4S)-1-(2-bromo-3,4,5-trimethoxyphenyl)-1-hepten-4-ol (123808-05-9)

Guidance literature:

Multi-step reaction with 15 steps

1: 82 percent / 1N H₂SO₄, NaNO₂ / H₂O / 1 h / 0 - 5 °C

2: 66 percent / LAH / diethyl ether / 1.) 0 deg C, then 3 h rt.

3: 1.) HBr; 2.) 50percent aq. KOH / 1.) AcOH, 1h; 2.) 120 deg C

4: aq. ethanol / 19 h / Heating

6: 83 percent / imidazole / dimethylformamide / 15 h / Ambient temperature

7: 95 percent / lithium borohydride, lithium triethylborohydride / diethyl ether; tetrahydrofuran / 3 h / Heating

8: pyridine / 3 h / 0 - 5 °C

9: 88 percent / NaI, NaHCO₃ / acetone / 2 h / Heating

10: 86 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

11: sodium acetate, bromine / 2 h / Ambient temperature

12: NaOH / methanol / 1 h / Ambient temperature

13: triethylamine / tetrahydrofuran / 2 h / 0 °C

14: DBU / benzene / 2 h / Heating

15: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature

With 1H-imidazole; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen bromide; bromine; sodium acetate; lithium triethylborohydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide; sodium nitrite; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; hexane; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/S0040-4020(01)80027-2

upstream raw materials:

(S)-(-)-1,2-pentanediol

L-Norvaline

2-(S)-hydroxyvaleric acid

(+)-(3S)-3-hydroxyhexanoic acid

Downstream raw materials:

6-((2S,3R,5S)-3-Hydroxy-5-propyl-tetrahydro-furan-2-yl)-2,3,4-trimethoxy-benzoic acid

monocerin

(2S,3aS,9bS)-6-Hydroxy-7,8-dimethoxy-2-propyl-2,3,3a,9b-tetrahydro-furo[3,2-c]isochromen-5-one

(2S,3R,5S)-5-Propyl-2-(3,4,5-trimethoxy-phenyl)-tetrahydro-furan-3-ol