5-(tert-Butyl-dimethyl-silanyloxy)-5-((Z)-6-iodo-hex-3-ene-1,5-diynyl)-2-methyl-cyclohex-1-enecarbaldehyde

Base Information

Chemical Name:5-(tert-Butyl-dimethyl-silanyloxy)-5-((Z)-6-iodo-hex-3-ene-1,5-diynyl)-2-methyl-cyclohex-1-enecarbaldehyde
CAS No.:213924-83-5
Molecular Formula:C₂₀H₂₇IO₂Si
Molecular Weight:454.423
Hs Code.:

Synonyms:5-(tert-Butyl-dimethyl-silanyloxy)-5-((Z)-6-iodo-hex-3-ene-1,5-diynyl)-2-methyl-cyclohex-1-enecarbaldehyde

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Chemical Property of 5-(tert-Butyl-dimethyl-silanyloxy)-5-((Z)-6-iodo-hex-3-ene-1,5-diynyl)-2-methyl-cyclohex-1-enecarbaldehyde

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Technology Process of 5-(tert-Butyl-dimethyl-silanyloxy)-5-((Z)-6-iodo-hex-3-ene-1,5-diynyl)-2-methyl-cyclohex-1-enecarbaldehyde

There total 10 articles about 5-(tert-Butyl-dimethyl-silanyloxy)-5-((Z)-6-iodo-hex-3-ene-1,5-diynyl)-2-methyl-cyclohex-1-enecarbaldehyde 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: 98.0%

: 213924-93-7
[5-(tert-Butyl-dimethyl-silanyloxy)-5-((Z)-6-iodo-hex-3-ene-1,5-diynyl)-2-methyl-cyclohex-1-enyl]-methanol

: 213924-83-5
5-(tert-Butyl-dimethyl-silanyloxy)-5-((Z)-6-iodo-hex-3-ene-1,5-diynyl)-2-methyl-cyclohex-1-enecarbaldehyde

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 21 ℃; for 1h;
DOI:10.1016/S0040-4039(98)01297-0

Reference yield:

: 4746-97-8
cyclohexanedione monoethylene ketal

: 213924-83-5
5-(tert-Butyl-dimethyl-silanyloxy)-5-((Z)-6-iodo-hex-3-ene-1,5-diynyl)-2-methyl-cyclohex-1-enecarbaldehyde

Guidance literature:: Multi-step reaction with 10 steps

1: 60 percent / LDA, HMPA / tetrahydrofuran / 0.5 h / -78 °C

2: 99 percent / KHMDS / tetrahydrofuran / 1 h / -78 - 21 °C

3: 99 percent / diethyl ether / -78 - 21 °C

4: 80 percent / 35percent aq. CF₃COOH / CHCl₃ / 72 h / 21 °C

5: 84 percent / t-BuLi, CeCl₃ / tetrahydrofuran / 0.17 h / -78 °C

6: 98 percent / Et₃N / CH₂Cl₂ / 0 - 21 °C

7: 99 percent / i-Bu₂AlH / CH₂Cl₂ / 2 h / -78 - -60 °C

8: 93 percent / n-Bu₄NF / tetrahydrofuran / 4 h / -78 - 0 °C

9: 69 percent / I₂, morpholine / benzene / 2 h / 60 °C

10: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 21 °C

With morpholine; N,N,N,N,N,N-hexamethylphosphoric triamide; cerium(III) chloride; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; benzene;
DOI:10.1016/S0040-4039(98)01297-0

Reference yield:

: 14160-65-7,77793-24-9,122090-88-4
ethyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate

: 213924-83-5
5-(tert-Butyl-dimethyl-silanyloxy)-5-((Z)-6-iodo-hex-3-ene-1,5-diynyl)-2-methyl-cyclohex-1-enecarbaldehyde

Guidance literature:: Multi-step reaction with 9 steps

1: 99 percent / KHMDS / tetrahydrofuran / 1 h / -78 - 21 °C

2: 99 percent / diethyl ether / -78 - 21 °C

3: 80 percent / 35percent aq. CF₃COOH / CHCl₃ / 72 h / 21 °C

4: 84 percent / t-BuLi, CeCl₃ / tetrahydrofuran / 0.17 h / -78 °C

5: 98 percent / Et₃N / CH₂Cl₂ / 0 - 21 °C

6: 99 percent / i-Bu₂AlH / CH₂Cl₂ / 2 h / -78 - -60 °C

7: 93 percent / n-Bu₄NF / tetrahydrofuran / 4 h / -78 - 0 °C

8: 69 percent / I₂, morpholine / benzene / 2 h / 60 °C

9: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 21 °C

With morpholine; cerium(III) chloride; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; benzene;
DOI:10.1016/S0040-4039(98)01297-0