methyl 3-(2-(((tert-butyldimethylsilyl)oxy)methyl)-1-hydroxy-3-methylcyclohex-2-en-1-yl)propiolate

Base Information

Chemical Name:methyl 3-(2-(((tert-butyldimethylsilyl)oxy)methyl)-1-hydroxy-3-methylcyclohex-2-en-1-yl)propiolate
CAS No.:1366469-92-2
Molecular Formula:C₁₈H₃₀O₄Si
Molecular Weight:338.519
Hs Code.:

Synonyms:methyl 3-(2-(((tert-butyldimethylsilyl)oxy)methyl)-1-hydroxy-3-methylcyclohex-2-en-1-yl)propiolate

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Chemical Property of methyl 3-(2-(((tert-butyldimethylsilyl)oxy)methyl)-1-hydroxy-3-methylcyclohex-2-en-1-yl)propiolate

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Technology Process of methyl 3-(2-(((tert-butyldimethylsilyl)oxy)methyl)-1-hydroxy-3-methylcyclohex-2-en-1-yl)propiolate

There total 3 articles about methyl 3-(2-(((tert-butyldimethylsilyl)oxy)methyl)-1-hydroxy-3-methylcyclohex-2-en-1-yl)propiolate 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%

: 1366469-87-5
2-(((tert-butyldimethylsilyl)oxy)methyl)-3-methylcyclohex-2-enone

: 922-67-8
propynoic acid methyl ester

: 1366469-92-2
methyl 3-(2-(((tert-butyldimethylsilyl)oxy)methyl)-1-hydroxy-3-methylcyclohex-2-en-1-yl)propiolate

Guidance literature:: propynoic acid methyl ester; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

2-(((tert-butyldimethylsilyl)oxy)methyl)-3-methylcyclohex-2-enone; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;
DOI:10.1016/j.bmcl.2012.01.006

Reference yield:

: 114908-48-4
4,6,7,8-tetrahydro-5H-benzo[d][1,3]dioxin-5-one

: 1366469-92-2
methyl 3-(2-(((tert-butyldimethylsilyl)oxy)methyl)-1-hydroxy-3-methylcyclohex-2-en-1-yl)propiolate

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetrahydrofuran; diethyl ether / 1 h / -78 °C

2.1: hydrogenchloride / tetrahydrofuran; diethyl ether / 0.33 h / 20 °C

3.1: dmap; triethylamine / dichloromethane / 2 h / 20 °C

4.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: 0.5 h / -78 °C

With hydrogenchloride; dmap; n-butyllithium; triethylamine; diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1016/j.bmcl.2012.01.006

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1366469-92-2
methyl 3-(2-(((tert-butyldimethylsilyl)oxy)methyl)-1-hydroxy-3-methylcyclohex-2-en-1-yl)propiolate

Guidance literature:: Multi-step reaction with 2 steps

1.1: dmap; triethylamine / dichloromethane / 2 h / 20 °C

2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 0.5 h / -78 °C

With dmap; n-butyllithium; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1016/j.bmcl.2012.01.006