(S)-1-[3,4-(methylenedioxy)phenyl]-1-ethanol

Base Information

• Chemical Name: (S)-1-[3,4-(methylenedioxy)phenyl]-1-ethanol
• CAS No.: 179237-91-3
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.177
• Mol file: 179237-91-3.mol

Synonyms:(S)-1-[3,4-(methylenedioxy)phenyl]-1-ethanol

Chemical Property of (S)-1-[3,4-(methylenedioxy)phenyl]-1-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-1-[3,4-(methylenedioxy)phenyl]-1-ethanol

There total 5 articles about (S)-1-[3,4-(methylenedioxy)phenyl]-1-ethanol 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: 54.0%

(S)-(-)-α-methyl-2-iodo-4,5-methylenedioxybenzyl alcohol (908118-84-3) + 4,4,5,5-tetramethyl-2-(2,3,4-trimethoxy-6-triethylsilanyloxymethyl-phenyl)-[1,3,2]dioxaborolane (638164-11-1) → 1-[6-(6-hydroxymethyl-2,3,4-trimethoxy-phenyl)-benzo[1,3]dioxol-5-yl]-ethanol + 1-[6-(6-hydroxymethyl-2,3,4-trimethoxy-phenyl)-benzo[1,3]dioxol-5-yl]-ethanol + (S)-1-[3,4-(methylenedioxy)phenyl]-1-ethanol (179237-91-3)

Guidance literature:

(S)-(-)-α-methyl-2-iodo-4,5-methylenedioxybenzyl alcohol; 4,4,5,5-tetramethyl-2-(2,3,4-trimethoxy-6-triethylsilanyloxymethyl-phenyl)-[1,3,2]dioxaborolane; With barium dihydroxide; DavePhos; palladium diacetate; In 1,4-dioxane; water; at 100 ℃; for 1h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.25h; Further stages.;

DOI:10.1002/chem.200601764

Reference yield:

1-benzo[1,3]dioxol-5-yl-ethanol (6329-73-3,91613-73-9,120523-14-0) → 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) + (S)-1-[3,4-(methylenedioxy)phenyl]-1-ethanol (179237-91-3)

Guidance literature:

With oxygen; caesium carbonate; (-)-sparteine; In toluene; tert-butyl alcohol; at 60 ℃; for 15h; under 760.051 Torr; optical yield given as %ee; Molecular sieve;

DOI:10.1002/chem.200902172

Reference yield:

2-iodo-1-(2-triethylsilyloxy)ethyl-3,4,5-trimethoxybenzene (908118-90-1) + (S)-(-)-α-methyl-2-iodo-4,5-methylenedioxybenzyl alcohol (908118-84-3) → 1-{6-[2,3,4-trimethoxy-6-(2-triethylsilanyloxy-ethyl)-phenyl]-benzo[1,3]dioxol-5-yl}-ethanol + 1-{6-[2,3,4-trimethoxy-6-(2-triethylsilanyloxy-ethyl)-phenyl]-benzo[1,3]dioxol-5-yl}-ethanol + (S)-1-[3,4-(methylenedioxy)phenyl]-1-ethanol (179237-91-3)

Guidance literature:

2-iodo-1-(2-triethylsilyloxy)ethyl-3,4,5-trimethoxybenzene; With pinacol borane; triethylamine; CyJohnPhos; palladium diacetate; In 1,4-dioxane; at 80 ℃; for 0.5h;

(S)-(-)-α-methyl-2-iodo-4,5-methylenedioxybenzyl alcohol; With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; barium dihydroxide; palladium diacetate; In 1,4-dioxane; water; at 100 ℃; for 2.5h; Title compound not separated from byproducts;

DOI:10.1002/anie.200600451

upstream raw materials:

2-iodo-1-(2-triethylsilyloxy)ethyl-3,4,5-trimethoxybenzene

(S)-(-)-α-methyl-2-iodo-4,5-methylenedioxybenzyl alcohol

4,4,5,5-tetramethyl-2-(2,3,4-trimethoxy-6-triethylsilanyloxymethyl-phenyl)-[1,3,2]dioxaborolane

(R)-(-)-α-methyl-2-iodo-4,5-methylenedioxybenzyl alcohol

Refernces

• 1、 Joncour, Agnes,Decor, Anne,Liu, Jian-Miao,Tran Huu Dau, Marie-Elise,Baudoin, Olivier. "Asymmetric synthesis of antimicrotubule biaryl hybrids of allocolchicine and steganacin". . p. 5450 - 5465. Retrieved 2008/03/12.