1-[3-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-phenoxymethyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone

Base Information

Chemical Name:1-[3-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-phenoxymethyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone
CAS No.:544455-52-9
Molecular Formula:C₃₁H₃₇NO₄Si
Molecular Weight:515.725
Hs Code.:

1-[3-(<i>tert</i>-butyl-diphenyl-silanyloxy)-2-(4-methoxy-phenoxymethyl)-3,6-dihydro-2<i>H</i>-pyridin-1-yl]-ethanone

Synonyms:1-[3-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-phenoxymethyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone

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Chemical Property of 1-[3-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-phenoxymethyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone

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Technology Process of 1-[3-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-phenoxymethyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone

There total 14 articles about 1-[3-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-phenoxymethyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone 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: 93.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 544455-51-8
1-[(2R,3S)-3-Hydroxy-2-(4-methoxy-phenoxymethyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone

: 544455-52-9
1-[3-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-phenoxymethyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone

Guidance literature:: With 1H-imidazole; TEA; In N,N-dimethyl-formamide; at 60 ℃; for 12h;
DOI:10.1016/S0040-4039(03)00218-1

Reference yield:

: 150-76-5
4-methoxy-phenol

: 544455-52-9
1-[3-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-phenoxymethyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone

Guidance literature:: Multi-step reaction with 14 steps

1: 70 percent / K₂OsO₄*2H₂O; (DHQD)2PHAL; LiOH / 2-methyl-propan-2-ol; H₂O / 8 h / 4 °C

2: 80 percent / NaH / dimethylformamide / 8 h / 0 °C

3: 100 percent / LiBH₄ / diethyl ether / 0.25 h

4: 100 percent / TEA; DMAP / CH₂Cl₂ / 4 h / 25 °C

5: 95 percent / KH; 18-crown-ether / tetrahydrofuran / 5 h / 25 °C

6: 100 percent / tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 25 °C

7: 90 percent / periodinane / CH₂Cl₂ / 1 h / 25 °C

8: 94 percent / LiBr; DBU / tetrahydrofuran / 2 h / 25 °C

9: 80 percent / Grubb's bis(tricyclohexylphosphinebenzylidene Ru(IV)Cl₂ / toluene / 2 h / 90 °C

10: 85 percent / trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 25 °C

11: 80 percent / DIPAD; Ph₃P / tetrahydrofuran / 2 h / 0 °C

12: 100 percent / K₂CO₃ / methanol / 5 h / 25 °C

13: 93 percent / imidazole; TEA / dimethylformamide / 12 h / 60 °C

With 1H-imidazole; dmap; lithium hydroxide; potassium osmate(VI); lithium borohydride; 18-crown-ether; TEA; tetrabutyl ammonium fluoride; potassium hydride; sodium hydride; potassium carbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropyl (E)-azodicarboxylate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; trifluoroacetic acid; lithium bromide; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 2: Sharpless asymmetric aminohydroxylation / 8: Dess-Martin oxidation / 9: Horner-Wadsworth-Emmons olefination / 10: ring closing metathesis / 12: Mitsunobu reaction;
DOI:10.1016/S0040-4039(03)00218-1

Reference yield:

: 544455-38-1
ethyl (2E)-4-(4-methoxyphenoxy)but-2-enoate

: 544455-52-9
1-[3-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-phenoxymethyl)-3,6-dihydro-2H-pyridin-1-yl]-ethanone

Guidance literature:: Multi-step reaction with 13 steps

1: 70 percent / K₂OsO₄*2H₂O; (DHQD)2PHAL; LiOH / 2-methyl-propan-2-ol; H₂O / 8 h / 4 °C

2: 80 percent / NaH / dimethylformamide / 8 h / 0 °C

3: 100 percent / LiBH₄ / diethyl ether / 0.25 h

4: 100 percent / TEA; DMAP / CH₂Cl₂ / 4 h / 25 °C

5: 95 percent / KH; 18-crown-ether / tetrahydrofuran / 5 h / 25 °C

6: 100 percent / tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 25 °C

7: 90 percent / periodinane / CH₂Cl₂ / 1 h / 25 °C

8: 94 percent / LiBr; DBU / tetrahydrofuran / 2 h / 25 °C

9: 80 percent / Grubb's bis(tricyclohexylphosphinebenzylidene Ru(IV)Cl₂ / toluene / 2 h / 90 °C

10: 85 percent / trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 25 °C

11: 80 percent / DIPAD; Ph₃P / tetrahydrofuran / 2 h / 0 °C

12: 100 percent / K₂CO₃ / methanol / 5 h / 25 °C

13: 93 percent / imidazole; TEA / dimethylformamide / 12 h / 60 °C

With 1H-imidazole; dmap; lithium hydroxide; potassium osmate(VI); lithium borohydride; 18-crown-ether; TEA; tetrabutyl ammonium fluoride; potassium hydride; sodium hydride; potassium carbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropyl (E)-azodicarboxylate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; trifluoroacetic acid; lithium bromide; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1: Sharpless asymmetric aminohydroxylation / 7: Dess-Martin oxidation / 8: Horner-Wadsworth-Emmons olefination / 9: ring closing metathesis / 11: Mitsunobu reaction;
DOI:10.1016/S0040-4039(03)00218-1