tert-butyl (3-formylbicyclo[1.1.1]pentane)acetate

Base Information

• Chemical Name: tert-butyl (3-formylbicyclo[1.1.1]pentane)acetate
• CAS No.: 1113001-80-1
• Molecular Formula: C₁₂H₁₈O₃
• Molecular Weight: 210.273
• Hs Code.: 2918999090
• Mol file: 1113001-80-1.mol

Synonyms:

Chemical Property of tert-butyl (3-formylbicyclo[1.1.1]pentane)acetate

Chemical Property:

• Boiling Point: 259.9±13.0 °C(Predicted)
• Density: 1?+-.0.06 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

Bicyclo[1.1.1]pentane-1-aceticacid,3-formyl-,1,1-dimethylethylester 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (3-formylbicyclo[1.1.1]pentane)acetate

There total 7 articles about tert-butyl (3-formylbicyclo[1.1.1]pentane)acetate 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: 76.0%

tert-butyl (3-(hydroxymethyl)bicyclo[1.1.1]pentyl)acetate (1113001-78-7) → tert-butyl (3-formylbicyclo[1.1.1]pentane)acetate (1113001-80-1)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/j.bmc.2008.11.015

Reference yield:

3‐(methoxycarbonyl)bicyclo[1.1.1]pentane‐1‐carboxylic acid (83249-10-9) → tert-butyl (3-formylbicyclo[1.1.1]pentane)acetate (1113001-80-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.5 h / -15 °C / Inert atmosphere

1.2: 24.5 h / -4 - 0 °C

1.3: 0.5 h / 20 °C / Sonication

2.1: dmap; di-tert-butyl dicarbonate / 7 h / 20 °C

3.1: water; sodium hydroxide / methanol / 72 h / 20 °C

4.1: borane-THF / tetrahydrofuran / 6 h / -15 °C

5.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C

With dmap; borane-THF; di-tert-butyl dicarbonate; water; chloroformic acid ethyl ester; Dess-Martin periodane; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; 1.1: Arndt-Eistert synthesis / 1.2: Arndt-Eistert synthesis / 1.3: Arndt-Eistert synthesis / 5.1: Dess-Martin oxidation;

DOI:10.1016/j.bmc.2008.11.015

Reference yield:

C11H14O6 → tert-butyl (3-formylbicyclo[1.1.1]pentane)acetate (1113001-80-1)

Guidance literature:

Multi-step reaction with 6 steps

1: tetrahydrofuran; acetonitrile / 24.5 h / -4 - 0 °C

2: water; silver benzoate; triethylamine / tetrahydrofuran / 0.5 h / 20 °C / Sonication

3: dmap; di-tert-butyl dicarbonate / 7 h / 20 °C

4: water; sodium hydroxide / methanol / 72 h / 20 °C

5: borane-THF / tetrahydrofuran / 6 h / -15 °C

6: Dess-Martin periodane / dichloromethane / 1 h / 0 °C

With dmap; borane-THF; di-tert-butyl dicarbonate; water; silver benzoate; Dess-Martin periodane; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 2: Wolff rearrangement / 6: Dess-Martin oxidation;

DOI:10.1016/j.bmc.2008.11.015

upstream raw materials:

C₉H₁₀N₂O₃

2-(3-methoxycarbonylbicyclo[1.1.1]pentane)acetic acid

methyl 3-(tert-butoxycarbonylmethyl)bicyclo[1.1.1]pentane-1-carboxylate

3-(tert-butoxycarbonylmethyl)bicyclo[1.1.1]pentane-1-carboxylic acid

Downstream raw materials:

C₂₁H₂₈N₂O₃

C₂₁H₂₈N₂O₃