toluene-4-sulfonic acid 4-[(2R,3S)-2,3-dihydro-(3-methyl-5-(1E)-1-propenylbenzofuran-2-yl)]phenyl ester

Base Information

• Chemical Name: toluene-4-sulfonic acid 4-[(2R,3S)-2,3-dihydro-(3-methyl-5-(1E)-1-propenylbenzofuran-2-yl)]phenyl ester
• CAS No.: 944249-92-7
• Molecular Formula: C₂₅H₂₄O₄S
• Molecular Weight: 420.529
• Mol file: 944249-92-7.mol

Synonyms:toluene-4-sulfonic acid 4-[(2R,3S)-2,3-dihydro-(3-methyl-5-(1E)-1-propenylbenzofuran-2-yl)]phenyl ester

Chemical Property of toluene-4-sulfonic acid 4-[(2R,3S)-2,3-dihydro-(3-methyl-5-(1E)-1-propenylbenzofuran-2-yl)]phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of toluene-4-sulfonic acid 4-[(2R,3S)-2,3-dihydro-(3-methyl-5-(1E)-1-propenylbenzofuran-2-yl)]phenyl ester

There total 12 articles about toluene-4-sulfonic acid 4-[(2R,3S)-2,3-dihydro-(3-methyl-5-(1E)-1-propenylbenzofuran-2-yl)]phenyl 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: 99.0%

toluene-4-sulfonic acid 4-[(2R,3S)-2,3-dihydro-(3-methyl-5-1-propenylbenzofuran-2-yl)]phenyl ester → toluene-4-sulfonic acid 4-[(2R,3S)-2,3-dihydro-(3-methyl-5-(1E)-1-propenylbenzofuran-2-yl)]phenyl ester (944249-92-7)

Guidance literature:

With bis(benzonitrile)palladium(II) dichloride; In dichloromethane; for 23h; optical yield given as %de; Inert atmosphere;

DOI:10.1039/b801858h

Reference yield: 98.0%

toluene-4-sulfonic acid 4-[(2R,3R)-2,3-dihydro-3-iodomethyl-5-(1-propenylbenzofuran-2-yl)]phenyl ester → toluene-4-sulfonic acid 4-[(2R,3S)-2,3-dihydro-(3-methyl-5-(1E)-1-propenylbenzofuran-2-yl)]phenyl ester (944249-92-7)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; optical yield given as %de; Inert atmosphere;

DOI:10.1039/b801858h

Reference yield:

toluene-4-sulfonic acid 4-[(1E)-3-hydroxy-1-propenyl]phenyl ester (944249-85-8) → toluene-4-sulfonic acid 4-[(2R,3S)-2,3-dihydro-(3-methyl-5-(1E)-1-propenylbenzofuran-2-yl)]phenyl ester (944249-92-7)

Guidance literature:

Multi-step reaction with 6 steps

1: (-)-diisopropyl tartrate; t-BuOOH; 4 Angstroem molecular sieves / Ti(OPr-i)4 / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -25 °C

2: 64 percent / aq. NaOH / 2.5 h / 70 °C

3: 100 percent / Et₃N / CH₂Cl₂ / 12 h / 20 °C

4: 71 percent / NaI / butan-2-one / 4 h / Heating

5: 69 percent / Bu₃SnH; AIBN / toluene / 2 h / 80 °C

6: t-BuLi / hexane; tetrahydrofuran / 2 h / 20 °C

With tert.-butylhydroperoxide; sodium hydroxide; (-)-diisopropyl tartrate; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tert.-butyl lithium; tri-n-butyl-tin hydride; triethylamine; sodium iodide; titanium(IV) isopropylate; In tetrahydrofuran; 2,2,4-trimethylpentane; hexane; dichloromethane; toluene; butanone; 1: Sharpless asymmetric epoxidation / 6: Wittig reaction;

DOI:10.1039/b704211f

upstream raw materials:

toluene-4-sulfonic acid 4-[(2S,3R)-2,3-dihydro-5-formyl-3-methylbenzofuran-2-yl]phenyl ester

ethyltriphenylphosphonium iodide

toluene-4-sulfonic acid 4-[(R)-1-(4-formyl-2-iodophenoxy)allyl]phenyl ester

(2E)-3-[4-(toluene-4-sulfonyloxy)phenyl]-2-propenoic acid ethyl ester

Downstream raw materials:

4-{(2R,3R)-3-methyl-5-[(E)prop-1-en-1-yl]-2,3-dihydrobenzofuran-2-yl}phenol

4-{(2S,3S)-3-methyl-5-[(E)prop-1-en-1-yl]-2,3-dihydrobenzofuran-2-yl}phenol