2-[(1S,2R)-1-methyl-2-(prop-1-en-2-yl)cyclobutyl]acetic acid

Base Information

• Chemical Name: 2-[(1S,2R)-1-methyl-2-(prop-1-en-2-yl)cyclobutyl]acetic acid
• CAS No.: 68225-44-5
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.236
• Mol file: 68225-44-5.mol

Synonyms:2-[(1S,2R)-1-methyl-2-(prop-1-en-2-yl)cyclobutyl]acetic acid

Chemical Property of 2-[(1S,2R)-1-methyl-2-(prop-1-en-2-yl)cyclobutyl]acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(1S,2R)-1-methyl-2-(prop-1-en-2-yl)cyclobutyl]acetic acid

There total 49 articles about 2-[(1S,2R)-1-methyl-2-(prop-1-en-2-yl)cyclobutyl]acetic acid 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: 74.0%

Methyltriphenylphosphonium bromide (1779-49-3) + 2-[(1S,2S)-2-acetyl-1-methylcyclobutyl]acetic acid (68225-42-3) → 2-[(1S,2R)-1-methyl-2-(prop-1-en-2-yl)cyclobutyl]acetic acid (68225-44-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1021/jacs.8b01011

Reference yield:

α-(1,1-dimethyl-2-propenyl)-2-methyl-1,3-dioxolane-2-ethanol (63305-89-5) → 2-[(1S,2R)-1-methyl-2-(prop-1-en-2-yl)cyclobutyl]acetic acid (68225-44-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / Amberlist A-15 / H₂O; acetone / 24 h / Ambient temperature

2: trimethylsylilmethylmagnesium chloride / 20 h / Ambient temperature

3: 90 percent / coprous trifluormethanesulphonate-benzene complex / diethyl ether / 65 h / Irradiation

4: 94 percent / pyridinium chlorochromate / Celite / CH₂Cl₂ / 4 h / Ambient temperature

5: 80 percent / hydroxylamine hydrochloride, potassium carbonate / ethanol / 3 h / Heating

6: 1.) phosphorous pentachloride, 2,6-lutidine, 2.) KOH / 1.) ether, 2.) ethylene glycol-triethylene glycol, dimethyl ether, 200 degC, 38 h

With 2,6-dimethylpyridine; potassium hydroxide; copper(I) trifluoromethanesulfonate benzene; trimethylsylilmethylmagnesium chloride; phosphorus pentachloride; hydroxylamine hydrochloride; potassium carbonate; pyridinium chlorochromate; Amberlist A-15; Celite; In diethyl ether; ethanol; dichloromethane; water; acetone;

DOI:10.1016/S0040-4020(01)96088-0

Reference yield:

(+/-)3,3-dimethylhept-1-en-4-ol-6-one (111455-68-6) → 2-[(1S,2R)-1-methyl-2-(prop-1-en-2-yl)cyclobutyl]acetic acid (68225-44-5)

Guidance literature:

Multi-step reaction with 5 steps

1: trimethylsylilmethylmagnesium chloride / 20 h / Ambient temperature

2: 90 percent / coprous trifluormethanesulphonate-benzene complex / diethyl ether / 65 h / Irradiation

3: 94 percent / pyridinium chlorochromate / Celite / CH₂Cl₂ / 4 h / Ambient temperature

4: 80 percent / hydroxylamine hydrochloride, potassium carbonate / ethanol / 3 h / Heating

5: 1.) phosphorous pentachloride, 2,6-lutidine, 2.) KOH / 1.) ether, 2.) ethylene glycol-triethylene glycol, dimethyl ether, 200 degC, 38 h

With 2,6-dimethylpyridine; potassium hydroxide; copper(I) trifluoromethanesulfonate benzene; trimethylsylilmethylmagnesium chloride; phosphorus pentachloride; hydroxylamine hydrochloride; potassium carbonate; pyridinium chlorochromate; Celite; In diethyl ether; ethanol; dichloromethane;

DOI:10.1016/S0040-4020(01)96088-0

upstream raw materials:

Methyltriphenylphosphonium bromide

2-[(1S,2S)-2-acetyl-1-methylcyclobutyl]acetic acid

(+/-)-3-oximino-1,4,4-trimethylbicyclo<3.2.0>heptane

Methylenetriphenylphosphorane

Downstream raw materials:

grandisol