(+/-)-allolaurinterol

Base Information

• Chemical Name: (+/-)-allolaurinterol
• CAS No.: 81624-20-6
• Molecular Formula: C₁₅H₁₉BrO
• Molecular Weight: 295.219

Synonyms:(+/-)-allolaurinterol

Chemical Property of (+/-)-allolaurinterol

Chemical Property:

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Technology Process of (+/-)-allolaurinterol

There total 12 articles about (+/-)-allolaurinterol 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: 93.0%

allolaurinterol tert-butyldimethylsilyl ether (81603-58-9) → (+/-)-allolaurinterol (81624-20-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.0333333h; Ambient temperature;

DOI:10.1021/jo00135a026

Reference yield:

(+/-)-5-chloro-5-methyl-2-cyclopentenone (19931-04-5) → (+/-)-allolaurinterol (81624-20-6)

Guidance literature:

Multi-step reaction with 11 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

9: 80 percent / Br₂, propylene oxide / 0.08 h

10: 1.) Zn, TiCl₄ / 1.) THF, 20 min, 2.) THF, 6 h

11: 93 percent / n-Bu₄NF / tetrahydrofuran / 0.03 h / Ambient temperature

With 1H-imidazole; potassium hydroxide; sodium hydroxide; dipyridinium dichromate; borane-THF; 2,2,6,6-tetramethylpiperidinyl-lithium; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; bromine; tert.-butyl lithium; titanium tetrachloride; methyloxirane; zinc; 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) → (+/-)-allolaurinterol (81624-20-6)

Guidance literature:

Multi-step reaction with 11 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

9: 80 percent / Br₂, propylene oxide / 0.08 h

10: 1.) Zn, TiCl₄ / 1.) THF, 20 min, 2.) THF, 6 h

11: 93 percent / n-Bu₄NF / tetrahydrofuran / 0.03 h / Ambient temperature

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

DOI:10.1021/jo00135a026

upstream raw materials:

allolaurinterol tert-butyldimethylsilyl ether

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

1-(methoxymethoxy)-3-methylbenzene

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

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