6-(4-tert-butyldiphenylsilyloxy-3-methylidenebutyl)-2,2-dimethyl-4H-1,3-dioxin-4-one

Base Information

• Chemical Name: 6-(4-tert-butyldiphenylsilyloxy-3-methylidenebutyl)-2,2-dimethyl-4H-1,3-dioxin-4-one
• CAS No.: 1228023-14-0
• Molecular Formula: C₂₇H₃₄O₄Si
• Molecular Weight: 450.65

Synonyms:6-(4-tert-butyldiphenylsilyloxy-3-methylidenebutyl)-2,2-dimethyl-4H-1,3-dioxin-4-one

Chemical Property of 6-(4-tert-butyldiphenylsilyloxy-3-methylidenebutyl)-2,2-dimethyl-4H-1,3-dioxin-4-one

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 6-(4-tert-butyldiphenylsilyloxy-3-methylidenebutyl)-2,2-dimethyl-4H-1,3-dioxin-4-one

There total 4 articles about 6-(4-tert-butyldiphenylsilyloxy-3-methylidenebutyl)-2,2-dimethyl-4H-1,3-dioxin-4-one 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: 67.0%

tert-butyl 7-tert-butyldiphenylsilanyloxy-6-methylidene-hept-3-one-ate (1228023-13-9) + acetic anhydride (108-24-7) → 6-(4-tert-butyldiphenylsilyloxy-3-methylidenebutyl)-2,2-dimethyl-4H-1,3-dioxin-4-one (1228023-14-0)

Guidance literature:

With trifluoroacetic acid; In acetone; for 22h;

DOI:10.1016/j.tet.2013.03.010

Reference yield: 67.0%

tert-butyl 7-tert-butyldiphenylsilanyloxy-6-methylidene-hept-3-one-ate (1228023-13-9) + acetone (67-64-1) → 6-(4-tert-butyldiphenylsilyloxy-3-methylidenebutyl)-2,2-dimethyl-4H-1,3-dioxin-4-one (1228023-14-0)

Guidance literature:

With acetic anhydride; trifluoroacetic acid; for 22h;

DOI:10.1021/ol1006373

Reference yield:

{[2-(bromomethyl)prop-2-en-1-yl]oxy}(tert-butyl)diphenylsilane (913253-34-6) → 6-(4-tert-butyldiphenylsilyloxy-3-methylidenebutyl)-2,2-dimethyl-4H-1,3-dioxin-4-one (1228023-14-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 0.83 h / 0 °C / Inert atmosphere

1.2: 3.92 h / -78 - 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / acetone / 22 h

With n-butyllithium; diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; hexane; acetone;

DOI:10.1016/j.tet.2013.03.010

upstream raw materials:

tert-butyl 7-tert-butyldiphenylsilanyloxy-6-methylidene-hept-3-one-ate

acetone

2-<(tert-butyldiphenylsilyloxy)methyl>prop-2-en-1-ol

{[2-(bromomethyl)prop-2-en-1-yl]oxy}(tert-butyl)diphenylsilane

Downstream raw materials:

C₃₀H₄₂O₄Si₂

(Z)-methyl 8,9-dihydro-7-hydroxy-8-(2-(tert-butyldiphenylsilyloxymethyl)allyl)-2,9,9-trimethyl-2H-cyclohepta[cd]indole-6-carboxylate

O-(tert-butyldiphenylsilyl)-2-methylene-4-(2,2-dimethyl-4H-1,3-dioxin-4-one-6-yl)-5-(4-bromo-1-methylindol-3-yl)-5-methyl-hexan-1-ol

3-oxo-4-[1',1'-dimethyl-1'-(4-bromo-1-methylindol-3-yl)-methyl]-6-methylene-7-(tert-butyldiphenylsilyloxy)-heptanoate methyl ester

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