(1R*)-1-but-3-enyl-4-hydroxy-2,6,6-trimethylcyclohex-2-enecarboxylic acid ethyl ester

Base Information

Chemical Name:(1R*)-1-but-3-enyl-4-hydroxy-2,6,6-trimethylcyclohex-2-enecarboxylic acid ethyl ester
CAS No.:1307740-43-7
Molecular Formula:C₁₆H₂₆O₃
Molecular Weight:266.381
Hs Code.:

Synonyms:(1R*)-1-but-3-enyl-4-hydroxy-2,6,6-trimethylcyclohex-2-enecarboxylic acid ethyl ester

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Chemical Property of (1R*)-1-but-3-enyl-4-hydroxy-2,6,6-trimethylcyclohex-2-enecarboxylic acid ethyl ester

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Technology Process of (1R*)-1-but-3-enyl-4-hydroxy-2,6,6-trimethylcyclohex-2-enecarboxylic acid ethyl ester

There total 5 articles about (1R*)-1-but-3-enyl-4-hydroxy-2,6,6-trimethylcyclohex-2-enecarboxylic acid ethyl ester 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: 79.0%

: 1307740-42-6
(1R*)-1-but-3-enyl-2,6,6-trimethyl-4-oxocyclohex-2-enecarboxylic acid ethyl ester

: 1307740-43-7
(1R*)-1-but-3-enyl-4-hydroxy-2,6,6-trimethylcyclohex-2-enecarboxylic acid ethyl ester

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride heptahydrate; In methanol; dichloromethane; at 0 ℃; for 1h; optical yield given as %de;
DOI:10.1055/s-0030-1258412

Reference yield:

: (1S*,2S*)-1-but-3-enyl-4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-3-enecarboxylic acid

: 1307740-43-7
(1R*)-1-but-3-enyl-4-hydroxy-2,6,6-trimethylcyclohex-2-enecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 2,6-dimethylpyridine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 24 h / 20 °C / Inert atmosphere

2: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol; dichloromethane / 1 h / 0 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; cerium(III) chloride heptahydrate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; benzene;
DOI:10.1055/s-0030-1258412

Reference yield:

: 759-58-0
ethyl isopropylidenecyanoacetate

: 1307740-43-7
(1R*)-1-but-3-enyl-4-hydroxy-2,6,6-trimethylcyclohex-2-enecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: zinc(II) chloride / toluene / 0.5 h / Inert atmosphere

1.2: 20 h / 80 °C / Inert atmosphere

2.1: lithium dihydronaphthylide radical / tetrahydrofuran / 0.5 h / -45 °C / Inert atmosphere

2.2: 12 h / 20 °C / Inert atmosphere

3.1: 2,6-dimethylpyridine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 24 h / 20 °C / Inert atmosphere

4.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol; dichloromethane / 1 h / 0 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; cerium(III) chloride heptahydrate; lithium dihydronaphthylide radical; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;
DOI:10.1055/s-0030-1258412