trans-2,3-dimethyl-3-<2-(tert-butyldimethylsiloxy)-4-methylphenyl>cyclopentanone

Base Information

• Chemical Name: trans-2,3-dimethyl-3-<2-(tert-butyldimethylsiloxy)-4-methylphenyl>cyclopentanone
• CAS No.: 81603-56-7
• Molecular Formula: C₂₀H₃₂O₂Si
• Molecular Weight: 332.558

Synonyms:trans-2,3-dimethyl-3-<2-(tert-butyldimethylsiloxy)-4-methylphenyl>cyclopentanone

Chemical Property of trans-2,3-dimethyl-3-<2-(tert-butyldimethylsiloxy)-4-methylphenyl>cyclopentanone

Chemical Property:

Purity/Quality:

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Technology Process of trans-2,3-dimethyl-3-<2-(tert-butyldimethylsiloxy)-4-methylphenyl>cyclopentanone

There total 9 articles about trans-2,3-dimethyl-3-<2-(tert-butyldimethylsiloxy)-4-methylphenyl>cyclopentanone 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: 94.0%

trans-2,3-dimethyl-3-<2-(tert-butyldimethylsiloxy)-4-methylphenyl>cyclopentanol (81603-55-6) → trans-2,3-dimethyl-3-<2-(tert-butyldimethylsiloxy)-4-methylphenyl>cyclopentanone (81603-56-7)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; for 4h; Ambient temperature;

DOI:10.1021/jo00135a026

Reference yield:

(+/-)-5-chloro-5-methyl-2-cyclopentenone (19931-04-5) → trans-2,3-dimethyl-3-<2-(tert-butyldimethylsiloxy)-4-methylphenyl>cyclopentanone (81603-56-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) t-BuLi / 1.) pentane, 0 deg C, 3 h, 2.) ether, -78 deg C, 6 h

2: 50 percent / KOH / methanol / 24 h / Heating

3: 1.) PCl₃ / 1.) ether, 0 deg C, 2 min

4: 83 percent / H₂ / Pt(IV) oxide / ethanol / 6 h

5: 65 percent / N-lithio-2,2,6,6-tetramethylpiperidide / tetrahydrofuran / 18 h / Heating

6: 96 percent / imidazole / dimethylformamide / 48 h / 40 °C

7: 1.) BH₃*THF, 2.) H₂O₂, aq. NaOH / 1.) THF, 0 deg C, 4 h, 2.) 1 h

8: 94 percent / pyridinium dichromate / dimethylformamide / 4 h / Ambient temperature

With 1H-imidazole; potassium hydroxide; sodium hydroxide; dipyridinium dichromate; borane-THF; 2,2,6,6-tetramethylpiperidinyl-lithium; hydrogen; dihydrogen peroxide; tert.-butyl lithium; phosphorus trichloride; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00135a026

Reference yield:

1-(methoxymethoxy)-3-methylbenzene (57234-27-2) → trans-2,3-dimethyl-3-<2-(tert-butyldimethylsiloxy)-4-methylphenyl>cyclopentanone (81603-56-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) t-BuLi / 1.) pentane, 0 deg C, 3 h, 2.) ether, -78 deg C, 6 h

2: 50 percent / KOH / methanol / 24 h / Heating

3: 1.) PCl₃ / 1.) ether, 0 deg C, 2 min

4: 83 percent / H₂ / Pt(IV) oxide / ethanol / 6 h

5: 65 percent / N-lithio-2,2,6,6-tetramethylpiperidide / tetrahydrofuran / 18 h / Heating

6: 96 percent / imidazole / dimethylformamide / 48 h / 40 °C

7: 1.) BH₃*THF, 2.) H₂O₂, aq. NaOH / 1.) THF, 0 deg C, 4 h, 2.) 1 h

8: 94 percent / pyridinium dichromate / dimethylformamide / 4 h / Ambient temperature

With 1H-imidazole; potassium hydroxide; sodium hydroxide; dipyridinium dichromate; borane-THF; 2,2,6,6-tetramethylpiperidinyl-lithium; hydrogen; dihydrogen peroxide; tert.-butyl lithium; phosphorus trichloride; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00135a026

upstream raw materials:

trans-2,3-dimethyl-3-<2-(tert-butyldimethylsiloxy)-4-methylphenyl>cyclopentanol

(+/-)-5-chloro-5-methyl-2-cyclopentenone

1-(methoxymethoxy)-3-methylbenzene

3a,8b-dihydro-3a,6,8b-trimethyl-3H-cyclopentabenzofuran

Downstream raw materials:

trans-2,3-dimethyl-3-<5-bromo-2-(tert-butyldimethylsiloxy)-4-methylphenyl>cyclopentanone

(+/-)-allolaurinterol

allolaurinterol tert-butyldimethylsilyl ether

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