4-methoxy-3-methyl-2(5H)-furanone

Base Information

• Chemical Name: 4-methoxy-3-methyl-2(5H)-furanone
• CAS No.: 27205-80-7
• Molecular Formula: C₆H₈O₃
• Molecular Weight: 128.128
• Mol file: 27205-80-7.mol

Synonyms:

Chemical Property of 4-methoxy-3-methyl-2(5H)-furanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-methoxy-3-methyl-2(5H)-furanone

There total 1 articles about 4-methoxy-3-methyl-2(5H)-furanone 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:

(4-methoxy-3-methyl-furan-2-yloxy)-trimethyl-silane + 5-(3-benzyloxy-propyl)-5-methoxy-1-(4-methoxy-benzyl)-pyrrolidin-2-one (360561-77-9) → 4-methoxy-3-methyl-2(5H)-furanone (27205-80-7) + 5-[3-Benzyloxy-prop-(Z)-ylidene]-1-(4-methoxy-benzyl)-pyrrolidin-2-one

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1016/S0040-4020(01)01138-3

Reference yield:

4-methoxy-3-methyl-2(5H)-furanone (27205-80-7) + (2S, 3S)-5-(tert-butyldiphenylsilyloxy)-3-methylpentane-1,2-diol (187458-29-3) → 5-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methyl-butyl]-4-methoxy-3-methyl-5H-furan-2-one (1026583-53-8)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃; for 0.333333h;

DOI:10.1021/jo961993f

Reference yield:

4-methoxy-3-methyl-2(5H)-furanone (27205-80-7) → (1'RS,2S,3R,4S,5S)-3-Benzyloxy-2-(1'-hydroxyethyl)-4-methoxy-5-methyltetrahydropyran

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) LDA / 1.) THF, hexane, -20 deg C, 20 min; -78 deg C, 2 h, 2.) 1 h

2: 100 percent / H₂, NaHCO₃ / 5percent Rh/Al₂O₃ / ethyl acetate / 8 h / 5320 Torr

3: 95 percent / aq. AcOH / tetrahydrofuran / 5 h / Ambient temperature

4: PPTS / CH₂Cl₂ / 0.25 h / Ambient temperature

5: 99.4 percent / LiBEt₃H / tetrahydrofuran / 1 h / Ambient temperature

6: DMAP, Et₃N / CH₂Cl₂ / 10 h / Ambient temperature

7: NaH, TBAI / tetrahydrofuran / 12 h / Ambient temperature

8: 100 percent / aq. AcOH / 3 h / Ambient temperature

9: 97 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

10: 100 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

11: 80 percent / aq. NaOH, TBAB / toluene / 1.5 h / 90 °C

12: 89 percent / aq. AcOH / 2 h / 60 °C

13: NaIO₄ / CH₂Cl₂; H₂O / 2 h / 0 °C

14: diethyl ether / 3 h / -78 °C

With dmap; sodium hydroxide; sodium periodate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium triethylborohydride; sodium hydrogencarbonate; acetic acid; triethylamine; lithium diisopropyl amide; Rh/Al₂O₃; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; toluene;

upstream raw materials:

5-(3-benzyloxy-propyl)-5-methoxy-1-(4-methoxy-benzyl)-pyrrolidin-2-one

Downstream raw materials:

5-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methyl-butyl]-4-methoxy-3-methyl-5H-furan-2-one

3-methyl-furan-2,4-dione

(2R,3R,4S,5S)-3-Benzyloxy-4-methoxy-5-methyl-tetrahydro-pyran-2-carbaldehyde

(2R,3R,4S,5S)-2-Acetyl-3-benzyloxy-4-methoxy-5-methyltetrahydropyran