methyl 5-(tert-butyldiphenylsilyloxy)-3-isopropylidene-2-oxocyclohexane-1-carboxylate

Base Information

• Chemical Name: methyl 5-(tert-butyldiphenylsilyloxy)-3-isopropylidene-2-oxocyclohexane-1-carboxylate
• CAS No.: 951386-56-4
• Molecular Formula: C₂₇H₃₄O₄Si
• Molecular Weight: 450.65
• Mol file: 951386-56-4.mol

Synonyms:methyl 5-(tert-butyldiphenylsilyloxy)-3-isopropylidene-2-oxocyclohexane-1-carboxylate

Chemical Property of methyl 5-(tert-butyldiphenylsilyloxy)-3-isopropylidene-2-oxocyclohexane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-(tert-butyldiphenylsilyloxy)-3-isopropylidene-2-oxocyclohexane-1-carboxylate

There total 2 articles about methyl 5-(tert-butyldiphenylsilyloxy)-3-isopropylidene-2-oxocyclohexane-1-carboxylate 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: 94.0%

2-isopropylidene-4-(tert-butyldiphenylsilyloxy)cyclohexanone (951386-29-1) + carbonic acid dimethyl ester (616-38-6) → methyl 5-(tert-butyldiphenylsilyloxy)-3-isopropylidene-2-oxocyclohexane-1-carboxylate (951386-56-4)

Guidance literature:

With potassium hydride; sodium hydride; In tetrahydrofuran; for 1h; Heating;

DOI:10.1021/jo071156l

Reference yield:

4-<(tert-Butyldiphenylsilyl)oxy>cyclohexanone (130745-59-4) → methyl 5-(tert-butyldiphenylsilyloxy)-3-isopropylidene-2-oxocyclohexane-1-carboxylate (951386-56-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium; HN(TMS)2; ZnCl₂ / tetrahydrofuran / 0.5 h / -78 °C

1.2: 75 percent / PTSA / benzene / 2 h / Heating

2.1: 94 percent / NaH; KH / tetrahydrofuran / 1 h / Heating

With n-butyllithium; potassium hydride; sodium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; zinc(II) chloride; In tetrahydrofuran;

DOI:10.1021/jo071156l

Reference yield: 72.0%

methyl 5-(tert-butyldiphenylsilyloxy)-3-isopropylidene-2-oxocyclohexane-1-carboxylate (951386-56-4) + 2-Methylphenylboronic acid (16419-60-6) → methyl 5-(tert-butyldiphenylsilyloxy)-3-isopropylidene-2-oxo-1-o-tolylcyclohexanecarboxylate

Guidance literature:

2-Methylphenylboronic acid; With lead(IV) acetate; mercury(II) trifluoroacetate; In chloroform; at 20 - 60 ℃;

methyl 5-(tert-butyldiphenylsilyloxy)-3-isopropylidene-2-oxocyclohexane-1-carboxylate; With pyridine; In chloroform; at 60 ℃; for 12h; Further stages.;

DOI:10.1021/jo071156l

upstream raw materials:

2-isopropylidene-4-(tert-butyldiphenylsilyloxy)cyclohexanone

carbonic acid dimethyl ester

4-<(tert-Butyldiphenylsilyl)oxy>cyclohexanone