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

Base Information

• Chemical Name: (1R,2S,3R)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol
• CAS No.: 146451-39-0
• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.305
• Mol file: 146451-39-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 30 articles about (1R,2S,3R)-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: 100.0%

(1R,2S,3R)-1,3-Dimethyl-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-3-vinylcyclohexanol (152492-32-5) → (1R,2S,3R)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol (146451-39-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 5h; Ambient temperature;

DOI:10.1021/jo00075a021

Reference yield: 57.0%

(3R/S,4S,5R)-5-Methyl-4-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-5-vinyl-1-oxaspiro<2.5>octane (146383-54-2) → (1R,2S,3R)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol (146451-39-0) + (1S,2S,3R)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol (146383-55-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; Heating;

DOI:10.1016/S0040-4039(00)74773-3

Reference yield:

(2'S,3aS,3'R,4'R,5'R,7aR)-2'-<(1R)-Dihydroxyethyl>-4',5'-(isopropylidenedioxy)spiro-2(3H)-one → (1R,2S,3R)-2-(2-Hydroxyethyl)-1,3-dimethyl-3-vinylcyclohexanol (146451-39-0)

Guidance literature:

Multi-step reaction with 13 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: conc. aq. HCl / 72 h / -15 °C

7: 52 percent / Raney nickel T-4 / ethanol / 13 h / Heating

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

9: tetrahydrofuran / 0.17 h / Ambient temperature

10: 100 percent / LiAlH₄ / tetrahydrofuran / 0.33 h / Ambient temperature

11: 1.) imidazole, 2.) PCC, molecular sieves / 1.) DMF, r.t., 1 h, 2.) CH₂Cl₂, r.t., 1 h

12: 82 percent / diethyl ether / 0.58 h / -78 °C

13: 100 percent / n-Bu₄NF / tetrahydrofuran / 5 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; molecular sieve; Raney nickel T-4; tetrabutyl ammonium fluoride; sodium hydride; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00075a021

upstream raw materials:

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

(3R/S,4S,5R)-5-Methyl-4-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>-5-vinyl-1-oxaspiro<2.5>octane

(2R,3R,4R,5S)-4-(2-hydroxyethyl)-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran

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