Tert-butyl (methyldiphenylsilyl)acetate

Base Information

• Chemical Name: Tert-butyl (methyldiphenylsilyl)acetate
• CAS No.: 77772-21-5
• Molecular Formula: C19H24O2Si
• Molecular Weight: 312.484
• DSSTox Substance ID: DTXSID90440517
• Mol file: 77772-21-5.mol

Synonyms:77772-21-5;t-butyl (methyldiphenylsilyl)acetate;TERT-BUTYL (METHYLDIPHENYLSILYL)ACETATE;DTXSID90440517

Chemical Property of Tert-butyl (methyldiphenylsilyl)acetate

Chemical Property:

• PSA: 26.30000
• LogP: 3.22110
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 312.154556538
• Heavy Atom Count: 22
• Complexity: 342

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C[Si](C)(C1=CC=CC=C1)C2=CC=CC=C2

Technology Process of Tert-butyl (methyldiphenylsilyl)acetate

There total 3 articles about Tert-butyl (methyldiphenylsilyl)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: 91.0%

acetic acid tert-butyl ester (540-88-5) + chloromethyldiphenylsilane (144-79-6) → tert-butyl α-(methyldiphenylsilyl)acetate (77772-21-5)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; 1.) -78 deg C, 40 min, 2.) -78 deg C, 1 h, room temperature;

Reference yield: 79.0%

(methyldiphenylsilyl)ketene (92177-88-3) + tert-butyl alcohol (75-65-0) → tert-butyl α-(methyldiphenylsilyl)acetate (77772-21-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.1021/acs.joc.9b01859 DOI:10.1021/acs.joc.9b01859

Reference yield:

chloromethyldiphenylsilane (144-79-6) → tert-butyl α-(methyldiphenylsilyl)acetate (77772-21-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / ethylbenzene; hexane; tetrahydrofuran / 3 h / -78 - 20 °C / Inert atmosphere

1.2: 4 h / 20 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

With boron trifluoride diethyl etherate; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; ethylbenzene;

DOI:10.1021/acs.joc.9b01859

upstream raw materials:

acetic acid tert-butyl ester

chloromethyldiphenylsilane

(methyldiphenylsilyl)ketene

tert-butyl alcohol

Downstream raw materials:

diphenylmethylsilylethylethanol

2-(Methyl-diphenyl-silanyl)-5-(6-methyl-1,4,8,11-tetraoxa-dispiro[4.1.4.2]tridec-6-yl)-pentanoic acid tert-butyl ester

tert-butyl-2-(diphenylmethylsilyl)propionate

5-(1-Methyl-2,5-dioxo-cyclopentyl)-2-(methyl-diphenyl-silanyl)-pentanoic acid tert-butyl ester