2-(4-Methyl-7-methylene-cyclohept-3-enyl)-ethanol

Base Information

Chemical Name:2-(4-Methyl-7-methylene-cyclohept-3-enyl)-ethanol
CAS No.:152487-04-2
Molecular Formula:C₁₁H₁₈O
Molecular Weight:166.263
Hs Code.:

Synonyms:2-(4-Methyl-7-methylene-cyclohept-3-enyl)-ethanol

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Chemical Property of 2-(4-Methyl-7-methylene-cyclohept-3-enyl)-ethanol

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Technology Process of 2-(4-Methyl-7-methylene-cyclohept-3-enyl)-ethanol

There total 1 articles about 2-(4-Methyl-7-methylene-cyclohept-3-enyl)-ethanol 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: 91.0%

: 173481-23-7
2-(2-Hydroxy-ethyl)-5-methyl-cyclohept-4-enone

: 19493-09-5
Methylenetriphenylphosphorane

: 152487-04-2
2-(4-Methyl-7-methylene-cyclohept-3-enyl)-ethanol

Guidance literature:: In dimethyl sulfoxide; at 23 ℃;
DOI:10.1021/jo00072a006

Reference yield:

: 152487-04-2
2-(4-Methyl-7-methylene-cyclohept-3-enyl)-ethanol

: C₃₂H₄₉NO₄Si

Guidance literature:: Multi-step reaction with 18 steps

1: 91 percent / ClCOCOCl, DMSO, Et₃N

3: 1.) Ph₃P, DEAD, PhCO₂H, 2.) K₂CO₃ / 1.) -20 to 23 deg C, 2.) MeOH

4: 1.) Red-Al, 2.) NIS / 1.) THF, 23 deg C, 2.) -70 to 23 deg C

5: imidazole / dimethylformamide

6: Ag₂CO₃ / Pd(OAc)2, Ph₃P / tetrahydrofuran / Heating

7: TBAF / tetrahydrofuran / 23 °C

8: 88 percent / TPAP, NMO / CH₂Cl₂; acetonitrile / 23 °C

9: 78 percent / Ni(acac)2, LiBr / diethyl ether / 23 °C

10: 91 percent / (OCH₂CH₂O)CHOMe, Amberlyst 15 / acetonitrile / 23 °C

11: m-CPBA, NaHCO₃ / CH₂Cl₂ / 0 °C

12: LiAlH₄ / tetrahydrofuran / 23 °C

13: 87 percent / 20percent aq. HCl / methanol / 65 °C

14: 77 percent / (i-Pr₂)NEt / CH₂Cl₂

16: 99 percent / LiAlH₄ / tetrahydrofuran / -78 °C

17: 97 percent / DMAP, pyridine / CH₂Cl₂ / 0 °C

18: LDA / tetrahydrofuran / 1.) 0 deg C, 2.) -78 to 0 deg C

With 2-methoxy-1,3-dioxolane; pyridine; 1H-imidazole; hydrogenchloride; dmap; bis(acetylacetonate)nickel(II); N-iodo-succinimide; lithium aluminium tetrahydride; N-methyl-2-indolinone; Amberlyst 15; tetrapropylammonium perruthennate; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; benzoic acid; silver carbonate; lithium bromide; lithium diisopropyl amide; diethylazodicarboxylate; palladium diacetate; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00072a006

Reference yield:

: 152487-04-2
2-(4-Methyl-7-methylene-cyclohept-3-enyl)-ethanol

: C₃₅H₄₄O₆

Guidance literature:: Multi-step reaction with 22 steps

1: 91 percent / ClCOCOCl, DMSO, Et₃N

3: 1.) Ph₃P, DEAD, PhCO₂H, 2.) K₂CO₃ / 1.) -20 to 23 deg C, 2.) MeOH

4: 1.) Red-Al, 2.) NIS / 1.) THF, 23 deg C, 2.) -70 to 23 deg C

5: imidazole / dimethylformamide

6: Ag₂CO₃ / Pd(OAc)2, Ph₃P / tetrahydrofuran / Heating

7: TBAF / tetrahydrofuran / 23 °C

8: 88 percent / TPAP, NMO / CH₂Cl₂; acetonitrile / 23 °C

9: 78 percent / Ni(acac)2, LiBr / diethyl ether / 23 °C

10: 91 percent / (OCH₂CH₂O)CHOMe, Amberlyst 15 / acetonitrile / 23 °C

11: m-CPBA, NaHCO₃ / CH₂Cl₂ / 0 °C

12: LiAlH₄ / tetrahydrofuran / 23 °C

13: 87 percent / 20percent aq. HCl / methanol / 65 °C

14: 77 percent / (i-Pr₂)NEt / CH₂Cl₂

16: 99 percent / LiAlH₄ / tetrahydrofuran / -78 °C

17: 97 percent / DMAP, pyridine / CH₂Cl₂ / 0 °C

18: LDA / tetrahydrofuran / 1.) 0 deg C, 2.) -78 to 0 deg C

19: KOH, K₂CO₃ / 140 °C

20: diethyl ether / 0 - 23 °C

21: DMAP, pyridine / 100 °C

22: 82 percent / HCl / methanol / 70 °C

With 2-methoxy-1,3-dioxolane; pyridine; 1H-imidazole; hydrogenchloride; dmap; bis(acetylacetonate)nickel(II); potassium hydroxide; N-iodo-succinimide; lithium aluminium tetrahydride; N-methyl-2-indolinone; Amberlyst 15; tetrapropylammonium perruthennate; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; benzoic acid; silver carbonate; lithium bromide; lithium diisopropyl amide; diethylazodicarboxylate; palladium diacetate; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00072a006