[10-bromo-11-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1,5-dioxa-spiro[5.5]undeca-7,10-dien-8-yl]-acetaldehyde

Base Information

Chemical Name:[10-bromo-11-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1,5-dioxa-spiro[5.5]undeca-7,10-dien-8-yl]-acetaldehyde
CAS No.:532393-18-3
Molecular Formula:C₂₈H₃₁BrO₅Si
Molecular Weight:555.541
Hs Code.:

[10-bromo-11-(<i>tert</i>-butyl-diphenyl-silanyloxymethyl)-9-oxo-1,5-dioxa-spiro[5.5]undeca-7,10-dien-8-yl]-acetaldehyde

Synonyms:[10-bromo-11-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1,5-dioxa-spiro[5.5]undeca-7,10-dien-8-yl]-acetaldehyde

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Chemical Property of [10-bromo-11-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1,5-dioxa-spiro[5.5]undeca-7,10-dien-8-yl]-acetaldehyde

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Technology Process of [10-bromo-11-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1,5-dioxa-spiro[5.5]undeca-7,10-dien-8-yl]-acetaldehyde

There total 17 articles about [10-bromo-11-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1,5-dioxa-spiro[5.5]undeca-7,10-dien-8-yl]-acetaldehyde 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: 62.0%

: 311312-52-4
8-bromo-7-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-10-(2-propenyl)-1,5-dioxospiro[5,5]undeca-7,10-dien-9-one

: 532393-18-3
[10-bromo-11-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1,5-dioxa-spiro[5.5]undeca-7,10-dien-8-yl]-acetaldehyde

Guidance literature:: With sodium periodate; osmium(VIII) oxide; In tetrahydrofuran; water; toluene; at 20 ℃; for 1.5h;
DOI:10.1021/ja021396c

Reference yield:

: 1194-98-5
2,5-Dihydroxybenzaldehyde

: 532393-18-3
[10-bromo-11-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1,5-dioxa-spiro[5.5]undeca-7,10-dien-8-yl]-acetaldehyde

Guidance literature:: Multi-step reaction with 10 steps

1.1: Br₂ / CHCl₃ / 20 °C

2.1: 10.64 g / imidazole / CH₂Cl₂ / 0.25 h / 20 °C

3.1: NaH / tetrahydrofuran / 0.5 h

3.2: 72 percent / DMA / tetrahydrofuran / 6 h / 65 °C

4.1: 100 percent / NaBH₄ / ethanol / 0.5 h / 0 °C

5.1: 93 percent / imidazole / dimethylformamide / 2 h / 20 °C

6.1: TBAF / tetrahydrofuran / 0.17 h / 0 °C

7.1: K₂CO₃ / dimethylformamide / 2.5 h / 20 °C

8.1: 2 h / 180 °C

8.2: 70 percent / PhI(OAc)2 / 0.33 h / 20 °C

9.1: 90 percent / pyridinium p-toluenesulfonate / benzene / 0.33 h / 80 °C

10.1: 62 percent / OsO₄; NaIO₄ / tetrahydrofuran; H₂O; toluene / 1.5 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; bromine; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; benzene; 8.1: Claisen rearrangement / 10.1: Lemieux-Johnson oxidation;
DOI:10.1021/ja021396c

Reference yield:

: 85432-87-7
2-bromo-3,6-dimethoxybenzaldehyde

: 532393-18-3
[10-bromo-11-(tert-butyl-diphenyl-silanyloxymethyl)-9-oxo-1,5-dioxa-spiro[5.5]undeca-7,10-dien-8-yl]-acetaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1.1: 1.42 g / conc. H₂SO₄ / 14 h / 70 °C

2.1: 96 percent / K₂CO₃ / dimethylformamide / 3 h

3.1: NaBH₄ / ethanol / 0.5 h / 20 °C

4.1: 94 percent / imidazole / dimethylformamide / 2.5 h / 20 °C

5.1: 2 h / 180 °C

5.2: 70 percent / PhI(OAc)2 / 0.33 h / 20 °C

6.1: 90 percent / pyridinium p-toluenesulfonate / benzene / 0.33 h / 80 °C

7.1: 62 percent / OsO₄; NaIO₄ / tetrahydrofuran; H₂O; toluene / 1.5 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sulfuric acid; pyridinium p-toluenesulfonate; potassium carbonate; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; toluene; benzene; 5.1: Claisen rearrangement / 7.1: Lemieux-Johnson oxidation;
DOI:10.1021/ja021396c