ethyl (E)-4-cyclohexyl-3-trimethylstannyl-2-butenoate

Base Information

Chemical Name:ethyl (E)-4-cyclohexyl-3-trimethylstannyl-2-butenoate
CAS No.:145384-06-1
Molecular Formula:C₁₅H₂₈O₂Sn
Molecular Weight:359.096
Hs Code.:

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of ethyl (E)-4-cyclohexyl-3-trimethylstannyl-2-butenoate

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Technology Process of ethyl (E)-4-cyclohexyl-3-trimethylstannyl-2-butenoate

There total 2 articles about ethyl (E)-4-cyclohexyl-3-trimethylstannyl-2-butenoate 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: 81.0%

: lithium (cyano)(trimethylstannyl)cuprate

: 145383-96-6
Ethyl 4-cyclohexyl-2-butynoate

: 145384-06-1,145384-01-6
ethyl (Z)-4-cyclohexyl-3-trimethylstannyl-2-butenoate

Guidance literature:: With ammonium hydroxide; ammonium chloride; In tetrahydrofuran; Ar atmosphere; dropwise addn. of soln. of ligand to soln. of 1.04 equiv. of cuprate (-48°C, stirring), stirring (-48°C for 2 h and 0°C for 2 h), addn. of aq. soln. NH4Cl/NH4OH, warming to room temp. (slow, air atmosphere), stirring; sepn. of org. phase, extn. of aq. layer (Et2O), washing of combined org. phases (brine), drying (MgSO4), concn., flash chromy. (silica gel, hexane/Et2O 97:3), distn. (104-107°C, 0.12 Torr); elem. anal.;

Reference yield: 81.0%

: lithium (cyano)(trimethylstannyl)cuprate

: 145383-96-6
Ethyl 4-cyclohexyl-2-butynoate

: 145384-06-1,145384-01-6
ethyl (E)-4-cyclohexyl-3-trimethylstannyl-2-butenoate

Guidance literature:: With ammonium hydroxide; ethanol; ammonium chloride; In tetrahydrofuran; Ar atmosphere; EtOH addn. (1.50 equiv.) to soln. of cuprate (1.50 equiv.), dropwise addn. of soln. of ligand (-78°C), stirring (-78°C for 7 h), addn. of aq. soln. NH4Cl/NH4OH, warming to room temp. (slow, air atmosphere), stirring; sepn. of org. phase, extn. of aq. layer (Et2O), washing of combined org. phases (brine), drying (MgSO4), concn., flash chromy. (silica gel, petroleum ether/Et2O 97:3), distn. (100-110°C, 0.12 Torr); elem. anal.;

Reference yield:

: 145384-06-1,145384-01-6
ethyl (Z)-4-cyclohexyl-3-trimethylstannyl-2-butenoate

: [(1R,6R)-6-Acetyl-3-methylene-bicyclohexyl-(2Z)-ylidene]-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

2: BF₃*Et₂O / CH₂Cl₂ / -78 °C

3: 1,3,5-trimethyl-benzene / Heating

With boron trifluoride diethyl etherate; In dichloromethane; 1,3,5-trimethyl-benzene;
DOI:10.1016/S0040-4039(00)91951-8