methyl (E)-3-[(E)-3-hydroxy-7-phenyl-1-hepten-1-yl]cyclohexylidene acetate

Base Information

Chemical Name:methyl (E)-3-[(E)-3-hydroxy-7-phenyl-1-hepten-1-yl]cyclohexylidene acetate
CAS No.:257866-98-1
Molecular Formula:C₂₂H₃₀O₃
Molecular Weight:342.478
Hs Code.:

Synonyms:methyl (E)-3-[(E)-3-hydroxy-7-phenyl-1-hepten-1-yl]cyclohexylidene acetate

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Chemical Property of methyl (E)-3-[(E)-3-hydroxy-7-phenyl-1-hepten-1-yl]cyclohexylidene acetate

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Technology Process of methyl (E)-3-[(E)-3-hydroxy-7-phenyl-1-hepten-1-yl]cyclohexylidene acetate

There total 9 articles about methyl (E)-3-[(E)-3-hydroxy-7-phenyl-1-hepten-1-yl]cyclohexylidene acetate 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:

: methyl (E)-3-[(E)-3-tert-butyldimethylsilyloxy-7-phenyl-1-hepten-1-yl]cyclohexylidene acetate

: 257866-98-1
methyl (E)-3-[(E)-3-hydroxy-7-phenyl-1-hepten-1-yl]cyclohexylidene acetate

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 64h;
DOI:10.1021/jm9910573

Reference yield:

: 65005-14-3
1,4-dioxa-spiro[4.5]decane-7-carbaldehyde

: 257866-98-1
methyl (E)-3-[(E)-3-hydroxy-7-phenyl-1-hepten-1-yl]cyclohexylidene acetate

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH

1.2: 86 percent / toluene / 16 h / 20 °C

2.1: 99.5 percent / cerium chloride heptahydrate; sodium borohydride / methanol / 4 h / 20 °C

3.1: 77.5 percent / silica gel; aq. H₂SO₄ / 16 h / 20 °C

4.1: 94 percent / DBU / CH₂Cl₂ / 48 h / 20 °C

5.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

5.2: 62 percent / tetrahydrofuran / 1 h / 60 °C

6.1: 1N aq. HCl / tetrahydrofuran / 64 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; sulfuric acid; silica gel; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; 1.1: Metallation / 1.2: Substitution / 2.1: Reduction / 3.1: Hydrolysis / 4.1: silylation / 5.1: Metallation / 5.2: Substitution / 6.1: Hydrolysis;
DOI:10.1021/jm9910573

Reference yield:

: 930-68-7
cyclohexenone

: 257866-98-1
methyl (E)-3-[(E)-3-hydroxy-7-phenyl-1-hepten-1-yl]cyclohexylidene acetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / hexane; diethyl ether / 2 h / -78 °C

1.2: cuprous 3-methoxy-3-methyl-but-1-ylide / hexane; diethyl ether / 0.5 h / -78 - -10 °C

1.3: 75 percent / tetrahydrofuran; hexane; diethyl ether / 2 h / -60 °C

2.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

2.2: 62 percent / tetrahydrofuran / 1 h / 60 °C

3.1: 1N aq. HCl / tetrahydrofuran / 64 h / 20 °C

With hydrogenchloride; n-butyllithium; sodium hydride; In tetrahydrofuran; diethyl ether; hexane; 1.1: Metallation / 1.2: Substitution / 1.3: Substitution / 2.1: Metallation / 2.2: Substitution / 3.1: Hydrolysis;
DOI:10.1021/jm9910573