3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}-1-propanol

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Chemical Name:3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}-1-propanol
CAS No.:273936-69-9
Molecular Formula:C₁₅H₂₆O₃
Molecular Weight:254.37
Hs Code.:

Synonyms:3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}-1-propanol

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Chemical Property of 3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}-1-propanol

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Technology Process of 3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}-1-propanol

There total 1 articles about 3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}-1-propanol 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: 89.0%

: 2-(3-{2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}propoxy)tetrahydro-2H-pyran

: 3-{(2Z)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}-1-propanol

: 273936-69-9
3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}-1-propanol

Guidance literature:: With methanol; toluene-4-sulfonic acid; at 20 ℃; for 3h;
DOI:10.1021/ja9939284

Reference yield:

: 273936-69-9
3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}-1-propanol

: benzyl (2R*,5R*,6R*)-6-[(3R*)-3-hydroxynonyl]-2-[(methoxymethoxy)methyl]-1-azaspiro[4,5]decane-1-carboxylate

Guidance literature:: Multi-step reaction with 13 steps

1.1: 80 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 83 percent / NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

3.1: 88 percent / diethyl ether / 0.5 h / 0 °C

4.1: 92 percent / NH₂OH*HCl; KOH / methanol / 2 h / 0 °C

5.1: 69 percent / aq. tetrabutylammonium periodate / methanol / 0.33 h / 0 °C

6.1: 95 percent / H₂ / Pd/C / methanol / 2 h / 760.05 Torr

7.1: 90 percent / Na/Hg; Na₂HPO₄; EtOH / 3 h / 0 °C

8.1: 89 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 0 °C

9.1: 91 percent / t-BuOK / tetrahydrofuran / 0.5 h / 20 °C

10.1: LiNH₂BH₃ / tetrahydrofuran; hexane / 4 h / 20 °C

11.1: 82.5 mg / aq. Na₂CO₃ / benzene / 12 h / 20 °C

12.1: 81 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

13.1: Mg / diethyl ether

13.2: 56 percent / diethyl ether / 4 h / 0 °C

With dmap; potassium hydroxide; sodium chlorite; disodium hydrogenphosphate; sodium dihydrogenphosphate; sodium amalgam; 2-methyl-but-2-ene; oxalyl dichloride; ethanol; lithium amidotrihydroborate; hydroxylamine hydrochloride; potassium tert-butylate; hydrogen; sodium carbonate; tetrabutylammonium periodite; magnesium; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol; benzene; 1.1: Swern oxidation / 2.1: Oxidation / 3.1: Esterification / 4.1: amidation / 5.1: oxidative Diels-Alder cycloaddition / 6.1: Catalytic hydrogenation / 7.1: Ring cleavage / 8.1: mesylation / 9.1: Cyclization / 10.1: reductive ring-opening / 11.1: Acylation / 12.1: Swern oxidation / 13.1: Grignard reaction / 13.2: Grignard reaction;
DOI:10.1021/ja9939284

Reference yield:

: 273936-69-9
3-{(2E)-2-[(2E)-4-(methoxymethyloxy)-2-butenylidene]cyclohexyl}-1-propanol

: (3R*,6R*,8aS*,12aS*)-3-(tert-butyldiphenylsilyl)oxy-6-hexyldodecahydropyrido[2,1-j]quinoline

Guidance literature:: Multi-step reaction with 19 steps

1.1: 80 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 83 percent / NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

3.1: 88 percent / diethyl ether / 0.5 h / 0 °C

4.1: 92 percent / NH₂OH*HCl; KOH / methanol / 2 h / 0 °C

5.1: 69 percent / aq. tetrabutylammonium periodate / methanol / 0.33 h / 0 °C

6.1: 95 percent / H₂ / Pd/C / methanol / 2 h / 760.05 Torr

7.1: 92 percent / aq. HCl / methanol / 0.5 h / Heating

8.1: 95 percent / NaH; Bu₄NI / dimethylformamide / 16 h / 20 °C

9.1: 96 percent / Na/Hg; Na₂HPO₄; EtOH / 6 h / 0 °C

10.1: 92 percent / imidazole / dimethylformamide / 16 h / 20 °C

11.1: 95 percent / H₂ / Pd/C / methanol / 4 h

12.1: 86 percent / Et₃N; DMAP / CH₂Cl₂ / 7 h / 0 °C

13.1: 99 percent / NaH / tetrahydrofuran / 1 h / Heating

14.1: LiNH₂BH₃ / tetrahydrofuran; hexane / 2 h / 20 °C

15.1: 34.0 mg / Na₂CO₃ / CHCl₃; tetrahydrofuran; H₂O / 16 h / 20 °C

16.1: 88 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

17.1: Mg / diethyl ether

17.2: diethyl ether / 3 h / 0 °C

18.1: 219 mg / PCC / CH₂Cl₂ / 2 h / 20 °C

19.1: 49 percent / H₂ / Pd/C / methanol / 5 h / 760.05 Torr

With 1H-imidazole; hydrogenchloride; dmap; potassium hydroxide; sodium chlorite; disodium hydrogenphosphate; sodium dihydrogenphosphate; sodium amalgam; 2-methyl-but-2-ene; oxalyl dichloride; ethanol; lithium amidotrihydroborate; hydroxylamine hydrochloride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium carbonate; tetrabutylammonium periodite; magnesium; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Swern oxidation / 2.1: Oxidation / 3.1: Esterification / 4.1: amidation / 5.1: oxidative Diels-Alder cycloaddition / 6.1: Catalytic hydrogenation / 7.1: Hydrolysis / 8.1: Etherification / 9.1: Ring cleavage / 10.1: silylation / 11.1: Hydrogenolysis / 12.1: Tosylation / 13.1: Cyclization / 14.1: reductive ring-opening / 15.1: Acylation / 16.1: Swern oxidation / 17.1: Grignard reaction / 17.2: Grignard reaction / 18.1: Oxidation / 19.1: Hydrogenolysis;
DOI:10.1021/ja9939284