methyl 4-methyl-2-<(phenylmethoxy)methyl>-3-furancarboxylate

Base Information

• Chemical Name: methyl 4-methyl-2-<(phenylmethoxy)methyl>-3-furancarboxylate
• CAS No.: 142041-29-0
• Molecular Formula: C₁₅H₁₆O₄
• Molecular Weight: 260.29
• Mol file: 142041-29-0.mol

Synonyms:

Chemical Property of methyl 4-methyl-2-<(phenylmethoxy)methyl>-3-furancarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-methyl-2-<(phenylmethoxy)methyl>-3-furancarboxylate

There total 1 articles about methyl 4-methyl-2-<(phenylmethoxy)methyl>-3-furancarboxylate 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:

Methyl 4-chloroacetoacetate (32807-28-6,935731-94-5) + dimethyl(prop-2-yn-1-yl)sulfonium bromide (23451-62-9) + benzyl alcohol (100-51-6,185532-71-2) → methyl 4-methyl-2-<(phenylmethoxy)methyl>-3-furancarboxylate (142041-29-0)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1021/jo00042a036

Reference yield:

methyl 4-methyl-2-<(phenylmethoxy)methyl>-3-furancarboxylate (142041-29-0) → 2-Benzyloxymethyl-4-methyl-furan-3-carboxylic acid (142041-30-3)

Guidance literature:

With lithium hydroxide; In methanol; for 72h; Ambient temperature;

DOI:10.1021/jo00042a036

Reference yield:

methyl 4-methyl-2-<(phenylmethoxy)methyl>-3-furancarboxylate (142041-29-0) → (3-endo,6-endo)-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-1-<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>heptan-2-one (142041-38-1)

Guidance literature:

Multi-step reaction with 8 steps

1: LiOH*H₂O / methanol / 72 h / Ambient temperature

2: copper-bronze, quinoline / 1 h / Heating

3: 98 percent / hydroquinone / CH₂Cl₂ / 312 h / 9050090 Torr

4: 1) 1 M aq. KOH, 2) 37percent aq. formaldehyde / 1) THF, water, r.t., 45 min, 2) 20 min

5: 95 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 1.5 h / -78 °C

6: 96 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

7: 1) borane-THF complex, 2) 5 M aq. NaOH, 30percent H₂O₂ / 1) THF, 0 deg C, 1 h, then r.t., 1 h, 2) reflux, 30 min

8: 89 percent / tetra-n-propylammonium perruthenate, N-methylmorpholine N-oxide, molecular sieves (3 Angstroem) / acetonitrile / 20 h / Ambient temperature

With 1H-imidazole; quinoline; potassium hydroxide; lithium hydroxide; sodium hydroxide; formaldehyd; tetrapropylammonium perruthennate; borane-THF; 3 A molecular sieve; dihydrogen peroxide; copper; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; hydroquinone; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00042a036

upstream raw materials:

Methyl 4-chloroacetoacetate

dimethyl(prop-2-yn-1-yl)sulfonium bromide

benzyl alcohol

Downstream raw materials:

2-Benzyloxymethyl-4-methyl-furan-3-carboxylic acid

4-methyl-2-<(phenylmethoxy)methyl>furan

endo-5-methyl-1-<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>hept-5-en-2-ol

5-methyl-1-<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>hept-5-en-2-one

Refernces