(+)-3-(tert-butyldimethylsilyloxy)-4-(3-acetoxy-5-methylphenyl)-1-butyne

Base Information

Chemical Name:(+)-3-(tert-butyldimethylsilyloxy)-4-(3-acetoxy-5-methylphenyl)-1-butyne
CAS No.:745809-29-4
Molecular Formula:C₁₉H₂₈O₃Si
Molecular Weight:332.515
Hs Code.:

Synonyms:(+)-3-(tert-butyldimethylsilyloxy)-4-(3-acetoxy-5-methylphenyl)-1-butyne

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (+)-3-(tert-butyldimethylsilyloxy)-4-(3-acetoxy-5-methylphenyl)-1-butyne

Chemical Property:

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Technology Process of (+)-3-(tert-butyldimethylsilyloxy)-4-(3-acetoxy-5-methylphenyl)-1-butyne

There total 9 articles about (+)-3-(tert-butyldimethylsilyloxy)-4-(3-acetoxy-5-methylphenyl)-1-butyne 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%

: 108-24-7
acetic anhydride

: 745809-55-6
(+)-3-[2-(tert-butyldimethylsilyloxy)but-3-ynyl]-5-methylphenol

: 745809-29-4
(+)-3-(tert-butyldimethylsilyloxy)-4-(3-acetoxy-5-methylphenyl)-1-butyne

Guidance literature:: With pyridine; at 23 ℃; for 18h;
DOI:10.1021/jo049426c

Reference yield:

: 58169-99-6
2,3,4,6-tetrabromo-5-methyl-phenol

: 745809-29-4
(+)-3-(tert-butyldimethylsilyloxy)-4-(3-acetoxy-5-methylphenyl)-1-butyne

Guidance literature:: Multi-step reaction with 8 steps

1: 2,6-lutidine

2: 92 percent / DDQ; buffer / CH₂Cl₂; H₂O / 1 h / pH 7

3: DMSO; oxalyl chloride; triethylamine / CH₂Cl₂ / 0.5 h / -78 - 0 °C

4: triphenylphosphine / CH₂Cl₂ / 0.08 h

5: 0.37 g / n-BuLi / tetrahydrofuran / 0.25 h / -78 °C

6: 99 percent / TBAF; acetic acid / tetrahydrofuran / 2 h

7: 98 percent / pyridine / 18 h / 23 °C

With pyridine; 2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; 4: Swern oxidation;
DOI:10.1021/jo049426c

Reference yield:

: 34946-83-3
2,4,4,6-tetrabromo-3-methyl-cyclohexa-2,5-dienone

: 745809-29-4
(+)-3-(tert-butyldimethylsilyloxy)-4-(3-acetoxy-5-methylphenyl)-1-butyne

Guidance literature:: Multi-step reaction with 9 steps

1: 57 percent / sulfuric acid / 16 h

2: 2,6-lutidine

3: 92 percent / DDQ; buffer / CH₂Cl₂; H₂O / 1 h / pH 7

4: DMSO; oxalyl chloride; triethylamine / CH₂Cl₂ / 0.5 h / -78 - 0 °C

5: triphenylphosphine / CH₂Cl₂ / 0.08 h

6: 0.37 g / n-BuLi / tetrahydrofuran / 0.25 h / -78 °C

7: 99 percent / TBAF; acetic acid / tetrahydrofuran / 2 h

8: 98 percent / pyridine / 18 h / 23 °C

With pyridine; 2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; sulfuric acid; tetrabutyl ammonium fluoride; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; 5: Swern oxidation;
DOI:10.1021/jo049426c