2-((tert-Butyldiphenylsilyl)oxy)-N-methoxy-N-methylacetamide

Base Information

• Chemical Name: 2-((tert-Butyldiphenylsilyl)oxy)-N-methoxy-N-methylacetamide
• CAS No.: 154698-93-8
• Molecular Formula: C20H27NO3Si
• Molecular Weight: 357.525
• DSSTox Substance ID: DTXSID30434713
• Wikidata: Q82249200
• Mol file: 154698-93-8.mol

Synonyms:2-((tert-Butyldiphenylsilyl)oxy)-N-methoxy-N-methylacetamide;154698-93-8;2-[tert-butyl(diphenyl)silyl]oxy-N-methoxy-N-methylacetamide;C20H27NO3Si;2-[(TERT-BUTYLDIPHENYLSILYL)OXY]-N-METHOXY-N-METHYLACETAMIDE;DTXSID30434713;MFCD14585077;AKOS016008926;DS-4979;CS-0130868;FT-0697747;I10460

Chemical Property of 2-((tert-Butyldiphenylsilyl)oxy)-N-methoxy-N-methylacetamide

Chemical Property:

• Boiling Point: 395.0±48.0 °C(Predicted)
• PSA: 38.77000
• Density: 1.07±0.1 g/cm3(Predicted)
• LogP: 2.58280
• Storage Temp.: Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 357.17602026
• Heavy Atom Count: 25
• Complexity: 405

Purity/Quality:

97% ^*data from raw suppliers

2-((tert-Butyldiphenylsilyl)oxy)-N-methoxy-N-methylacetamide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-((tert-Butyldiphenylsilyl)oxy)-N-methoxy-N-methylacetamide

There total 4 articles about 2-((tert-Butyldiphenylsilyl)oxy)-N-methoxy-N-methylacetamide 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: 97.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + methyl 2-((tert-butyl(diphenyl)silyl)oxy)acetate (154698-92-7) → 2-((tertbutyldiphenylsilyl)oxy)-N-methoxy-N-methylacetamide (154698-93-8)

Guidance literature:

With trimethylaluminum; In hexane; dichloromethane; 1.) -15 deg C, 30 min; room temp., 35 min, 2.) room temp., 2 h;

DOI:10.1021/jo00080a014

Reference yield: 85.0%

2-((t-butyldiphenylsilyl)oxy)acetic acid (76271-74-4) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → 2-((tertbutyldiphenylsilyl)oxy)-N-methoxy-N-methylacetamide (154698-93-8)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; Reflux;

DOI:10.1016/j.bmc.2010.12.036

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 2-((tertbutyldiphenylsilyl)oxy)-N-methoxy-N-methylacetamide (154698-93-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / imidazole, DMAP / dimethylformamide / 10 h / Ambient temperature

2: 97 percent / Me₃Al / CH₂Cl₂; hexane / 1.) -15 deg C, 30 min; room temp., 35 min, 2.) room temp., 2 h

With 1H-imidazole; dmap; trimethylaluminum; In hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00080a014

upstream raw materials:

N,O-dimethylhydroxylamine*hydrochloride

methyl 2-((tert-butyl(diphenyl)silyl)oxy)acetate

tert-butylchlorodiphenylsilane

2-((t-butyldiphenylsilyl)oxy)acetic acid

Downstream raw materials:

(tert-Butyldiphenylsiloxy)methyl 2-<(methoxymethyl)oxy>-4-methylphenyl ketone

(tert-Butyldiphenylsiloxy)methyl 3,4-dimethoxyphenyl ketone

1-(tert-butyldiphenylsiloxy)hex-5-en-2-one

(E)-1-(tert-Butyl-diphenyl-silanyloxy)-7,7-dimethoxy-4-methyl-hept-3-en-2-one