2(3H)-Furanone, 5-acetyldihydro-4-methyl-, (4S-cis)- (9CI)

Base Information

• Chemical Name: 2(3H)-Furanone, 5-acetyldihydro-4-methyl-, (4S-cis)- (9CI)
• CAS No.: 155322-90-0
• Molecular Formula: C₇H₁₀O₃
• Molecular Weight: 142.155
• Mol file: 155322-90-0.mol

Synonyms:2(3H)-Furanone, 5-acetyldihydro-4-methyl-, (4S-cis)- (9CI)

Chemical Property of 2(3H)-Furanone, 5-acetyldihydro-4-methyl-, (4S-cis)- (9CI)

Chemical Property:

• PSA: 43.37000
• LogP: 0.52700

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2(3H)-Furanone, 5-acetyldihydro-4-methyl-, (4S-cis)- (9CI)

There total 9 articles about 2(3H)-Furanone, 5-acetyldihydro-4-methyl-, (4S-cis)- (9CI) 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: 88.0%

(4S,5R)-5-((S)-1-Hydroxy-ethyl)-4-methyl-dihydro-furan-2-one → (4S,5R)-5-Acetyl-4-methyl-dihydro-furan-2-one (155322-90-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(00)61535-6

Reference yield:

(3S,4R)-3,4-(isopropylidenedioxy)-2-propanone (144829-98-1) → (4S,5R)-5-Acetyl-4-methyl-dihydro-furan-2-one (155322-90-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 97 percent / tetrahydrofuran / -78 °C

2: 74 percent / aq. AcOH / 60 °C

3: 100 percent / pyridine / CH₂Cl₂ / 0 °C

4: Et₃N / CH₂Cl₂ / 0.5 h / -15 °C

5: Et₃N / 2 h / -15 deg C up to RT

6: 83 percent / H₂ / Rh/Al₂O₃ / ethyl acetate / 2585.7 Torr

7: 72 percent / 2percent aq, HF / acetonitrile / Ambient temperature

8: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

With pyridine; hydrogen fluoride; hydrogen; Dess-Martin periodane; acetic acid; triethylamine; Rh/Al₂O₃; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4039(00)61535-6

Reference yield:

(S)-4-Hydroxy-5-((S)-1-hydroxy-ethyl)-4-methyl-dihydro-furan-2-one → (4S,5R)-5-Acetyl-4-methyl-dihydro-furan-2-one (155322-90-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / pyridine / CH₂Cl₂ / 0 °C

2: Et₃N / CH₂Cl₂ / 0.5 h / -15 °C

3: Et₃N / 2 h / -15 deg C up to RT

4: 83 percent / H₂ / Rh/Al₂O₃ / ethyl acetate / 2585.7 Torr

5: 72 percent / 2percent aq, HF / acetonitrile / Ambient temperature

6: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

With pyridine; hydrogen fluoride; hydrogen; Dess-Martin periodane; triethylamine; Rh/Al₂O₃; In dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4039(00)61535-6

upstream raw materials:

(3S,4R)-3,4-(isopropylidenedioxy)-2-propanone

(4S,5R)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-dihydro-furan-2-one

(R)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-5H-furan-2-one

Refernces