[1-(tert-Butyl-dimethyl-silanyloxy)-4-chloromethyl-cyclohex-3-enyl]-propynal

Base Information

Chemical Name:[1-(tert-Butyl-dimethyl-silanyloxy)-4-chloromethyl-cyclohex-3-enyl]-propynal
CAS No.:155136-32-6
Molecular Formula:C₁₆H₂₅ClO₂Si
Molecular Weight:312.912
Hs Code.:

Synonyms:[1-(tert-Butyl-dimethyl-silanyloxy)-4-chloromethyl-cyclohex-3-enyl]-propynal

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Chemical Property of [1-(tert-Butyl-dimethyl-silanyloxy)-4-chloromethyl-cyclohex-3-enyl]-propynal

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Technology Process of [1-(tert-Butyl-dimethyl-silanyloxy)-4-chloromethyl-cyclohex-3-enyl]-propynal

There total 9 articles about [1-(tert-Butyl-dimethyl-silanyloxy)-4-chloromethyl-cyclohex-3-enyl]-propynal 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: 74.0%

: 68-12-2,33513-42-7
N,N-dimethyl-formamide

: 155136-31-5
4-t-butyldimethylsilyloxy-1-chloromethyl-4-ethynylcyclohex-1-ene

: 155136-32-6
[1-(tert-Butyl-dimethyl-silanyloxy)-4-chloromethyl-cyclohex-3-enyl]-propynal

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 3h;
DOI:10.1016/S0040-4020(01)80630-X

Reference yield:

: 54584-38-2
methyl 1,4-dioxaspiro<4,5>dec-7-ene-8-carboxylate

: 155136-32-6
[1-(tert-Butyl-dimethyl-silanyloxy)-4-chloromethyl-cyclohex-3-enyl]-propynal

Guidance literature:: Multi-step reaction with 9 steps

1: 77 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

2: 97 percent / pyridine / 0 - 4 °C

3: 96 percent / 35percent aqueous TFA / CHCl₃ / 36 h

4: 88 percent / tetrahydrofuran / 3 h / -78 °C

5: 95 percent / TBAF*3H₂O / tetrahydrofuran / 2 h / 0 °C

6: 89 percent / CH₂Cl₂ / 2 h / 0 °C

7: DIBAL-H / CH₂Cl₂; hexane / 0.33 h / -78 °C

8: 79 percent / LiCl, MsCl, 2,6-lutidine / dimethylformamide / 2.5 h / 0 °C

9: 74 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 °C

With pyridine; 2,6-dimethylpyridine; lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; methanesulfonyl chloride; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)80630-X

Reference yield:

: 72445-21-7
1,4-dioxaspiro-<4,5>dec-7-ene-8-methanol

: 155136-32-6
[1-(tert-Butyl-dimethyl-silanyloxy)-4-chloromethyl-cyclohex-3-enyl]-propynal

Guidance literature:: Multi-step reaction with 8 steps

1: 97 percent / pyridine / 0 - 4 °C

2: 96 percent / 35percent aqueous TFA / CHCl₃ / 36 h

3: 88 percent / tetrahydrofuran / 3 h / -78 °C

4: 95 percent / TBAF*3H₂O / tetrahydrofuran / 2 h / 0 °C

5: 89 percent / CH₂Cl₂ / 2 h / 0 °C

6: DIBAL-H / CH₂Cl₂; hexane / 0.33 h / -78 °C

7: 79 percent / LiCl, MsCl, 2,6-lutidine / dimethylformamide / 2.5 h / 0 °C

8: 74 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 °C

With pyridine; 2,6-dimethylpyridine; n-butyllithium; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; methanesulfonyl chloride; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)80630-X