(1R,2S,3S)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol

Base Information

Chemical Name:(1R,2S,3S)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol
CAS No.:152611-89-7
Molecular Formula:C₁₂H₂₂O₂
Molecular Weight:198.305
Hs Code.:

Synonyms:(1R,2S,3S)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol

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Chemical Property of (1R,2S,3S)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol

Chemical Property:

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Technology Process of (1R,2S,3S)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol

There total 32 articles about (1R,2S,3S)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol 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: 91.0%

: 152611-84-2
(1R,2S,3S)-1,3-Dimethyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanol

: 152611-89-7
(1R,2S,3S)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 6h; Ambient temperature;
DOI:10.1021/jo00075a021

Reference yield:

: 146383-48-4
(2R,3R,4R,5S)-4-(4-Hydroxybutyl)-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran

: 152611-89-7
(1R,2S,3S)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol

Guidance literature:: Multi-step reaction with 26 steps

1: imidazole / dimethylformamide / 8 h / Ambient temperature

2: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 5 h, 2.) -78 deg C, 1 h

3: 1.) KN(TMS)2, 18-crown-6 / 1.) THF, toluene, -78 deg C, 20 min, 2.) THF, 5 deg C, 14 h

4: 100 percent / n-Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

5: 95 percent / PCC, molecular sieves / CH₂Cl₂ / 0.5 h / Ambient temperature

6: Sm(II) iodide, HMPA, 2-propanol / tetrahydrofuran / 1 h / Ambient temperature

7: 80 percent / 1M aq. HCl / tetrahydrofuran / 28 h / 5 °C

8: aq. NaIO₄ / methanol / 0.83 h / Ambient temperature

9: NaBH₄ / methanol / 0.67 h / 0 °C

10: 89 percent / NaH / dimethylformamide / 2 h / Ambient temperature

11: 77 percent / 60percent aq. TFA / 72 h / 5 °C

12: aq. NaIO₄ / methanol / 4 h / Ambient temperature

13: NaBH₄ / methanol / 0.5 h / Ambient temperature

14: 83 percent / imidazole / dimethylformamide / 1.) r.t., 18 h, 2.) 50 deg C, 9 h

15: 85 percent / H₂ / Pd/C / ethanol / 26 h

16: aq. NaIO₄ / methanol / 0.75 h / Ambient temperature

17: conc. aq. HCl / 72 h / -15 °C

18: 95 percent / Raney nickel T-4 / ethanol / 6.5 h / Heating

19: 85 percent / n-Bu₄NF / tetrahydrofuran / 10 h / Ambient temperature

20: PCC, molecular sieves / CH₂Cl₂ / 0.83 h / Ambient temperature

21: tetrahydrofuran / 0.17 h / Ambient temperature

22: 99 percent / LiAlH₄ / tetrahydrofuran / 0.33 h / Ambient temperature

23: imidazole / dimethylformamide / 14.5 h

24: PCC, molecular sieves / CH₂Cl₂ / 1.25 h / Ambient temperature

25: 74 percent / diethyl ether / 0.33 h / -15 °C

26: 91 percent / n-Bu₄NF / tetrahydrofuran / 6 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; molecular sieve; samarium diiodide; 18-crown-6 ether; Raney nickel T-4; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; sodium hydride; ozone; triphenylphosphine; isopropyl alcohol; pyridinium chlorochromate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00075a021

Reference yield:

: (2'S,3aS,3'R,4'R,5'R,7aR)-2'-<(1R)-Dihydroxyethyl>-4',5'-(isopropylidenedioxy)spiro-2(3H)-one

: 152611-89-7
(1R,2S,3S)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol

Guidance literature:: Multi-step reaction with 19 steps

1: aq. NaIO₄ / methanol / 0.83 h / Ambient temperature

2: NaBH₄ / methanol / 0.67 h / 0 °C

3: 89 percent / NaH / dimethylformamide / 2 h / Ambient temperature

4: 77 percent / 60percent aq. TFA / 72 h / 5 °C

5: aq. NaIO₄ / methanol / 4 h / Ambient temperature

6: NaBH₄ / methanol / 0.5 h / Ambient temperature

7: 83 percent / imidazole / dimethylformamide / 1.) r.t., 18 h, 2.) 50 deg C, 9 h

8: 85 percent / H₂ / Pd/C / ethanol / 26 h

9: aq. NaIO₄ / methanol / 0.75 h / Ambient temperature

10: conc. aq. HCl / 72 h / -15 °C

11: 95 percent / Raney nickel T-4 / ethanol / 6.5 h / Heating

12: 85 percent / n-Bu₄NF / tetrahydrofuran / 10 h / Ambient temperature

13: PCC, molecular sieves / CH₂Cl₂ / 0.83 h / Ambient temperature

14: tetrahydrofuran / 0.17 h / Ambient temperature

15: 99 percent / LiAlH₄ / tetrahydrofuran / 0.33 h / Ambient temperature

16: imidazole / dimethylformamide / 14.5 h

17: PCC, molecular sieves / CH₂Cl₂ / 1.25 h / Ambient temperature

18: 74 percent / diethyl ether / 0.33 h / -15 °C

19: 91 percent / n-Bu₄NF / tetrahydrofuran / 6 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; molecular sieve; Raney nickel T-4; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; pyridinium chlorochromate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00075a021