1-{3-[6-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-3-methylene-hexyl]-2,2,4-trimethyl-cyclohex-3-enyl}-prop-2-yn-1-ol

Base Information

• Chemical Name: 1-{3-[6-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-3-methylene-hexyl]-2,2,4-trimethyl-cyclohex-3-enyl}-prop-2-yn-1-ol
• CAS No.: 216978-41-5
• Molecular Formula: C₃₆H₅₀O₃Si
• Molecular Weight: 558.877
• Mol file: 216978-41-5.mol

Synonyms:1-{3-[6-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-3-methylene-hexyl]-2,2,4-trimethyl-cyclohex-3-enyl}-prop-2-yn-1-ol

Chemical Property of 1-{3-[6-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-3-methylene-hexyl]-2,2,4-trimethyl-cyclohex-3-enyl}-prop-2-yn-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{3-[6-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-3-methylene-hexyl]-2,2,4-trimethyl-cyclohex-3-enyl}-prop-2-yn-1-ol

There total 23 articles about 1-{3-[6-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-3-methylene-hexyl]-2,2,4-trimethyl-cyclohex-3-enyl}-prop-2-yn-1-ol 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: 97.0%

ethynylmagnesium chloride (65032-27-1) + 3-[6-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-3-methylene-hexyl]-2,2,4-trimethyl-cyclohex-3-enecarbaldehyde (216978-38-0) → 1-{3-[6-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-3-methylene-hexyl]-2,2,4-trimethyl-cyclohex-3-enyl}-prop-2-yn-1-ol (216978-41-5)

Guidance literature:

In tetrahydrofuran; 1.) -78 deg C, 1 h, 2.) -78 to -30 deg C, 1 h;

DOI:10.1039/a805268i

Reference yield:

ethyl 2-acetyl-3-methylbut-2-enoate (35044-52-1) → 1-{3-[6-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-3-methylene-hexyl]-2,2,4-trimethyl-cyclohex-3-enyl}-prop-2-yn-1-ol (216978-41-5)

Guidance literature:

Multi-step reaction with 14 steps

1: 98 percent / tetrahydrofuran / Ambient temperature

2: 92 percent / DIBAL-H / toluene / -60 °C

3: 93 percent / PTSA / benzene / 65 °C

4: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

5: 79 percent / BF₃*OEt₂ / toluene / 1.) -78 deg C, 5 min, 2.) -78 deg C, 10 h

6: 98 percent / NaBH₄ / methanol; diethyl ether / 1.) 0 deg C, 30 min, 2.) 0 deg C to r.t., 20 min

7: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / 0 - 20 °C

8: 95 percent / K₂CO₃ / methanol / 14 h / Ambient temperature

9: 97 percent / tetra(n-propyl)ammonium perruthenate, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

10: 82 percent / NaI, SnCl₂*2H₂O / dimethylformamide / 4 h / Ambient temperature

11: 97 percent / KHMDS / tetrahydrofuran / 1.) -78 deg C, 7 min, 2.) -78 deg C to r.t., 30 min

12: 88 percent / PPTS / methanol / 4.5 h / Ambient temperature

13: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / Ambient temperature

14: 97 percent / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 to -30 deg C, 1 h

With dmap; sodium tetrahydroborate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; sodium iodide; tin(ll) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1039/a805268i

Reference yield:

pent-1-yn-5-ol (5390-04-5) → 1-{3-[6-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-3-methylene-hexyl]-2,2,4-trimethyl-cyclohex-3-enyl}-prop-2-yn-1-ol (216978-41-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 99 percent / DMAP, Et₃N / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 14 h

2: 1.) 9-BBN, 2.) NaOH, H₂O, H₂O₂ / 1.) CH₂Cl₂, 0 deg C to r.t., 14 h, 2.) 0 deg C, 3 h

3: 82 percent / t-BuLi / tetrahydrofuran; diethyl ether / 1.) -110 deg C, 1 h, 2.) -110 deg C to r.t., 1 h

4: 99 percent / NaBH₄, CeCl₃*7H₂O / methanol / 0.33 h / 0 °C

5: 99 percent / NBS, PPh₃ / CH₂Cl₂ / 0.33 h / 0 - 20 °C

6: 82 percent / NaI, SnCl₂*2H₂O / dimethylformamide / 4 h / Ambient temperature

7: 97 percent / KHMDS / tetrahydrofuran / 1.) -78 deg C, 7 min, 2.) -78 deg C to r.t., 30 min

8: 88 percent / PPTS / methanol / 4.5 h / Ambient temperature

9: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / Ambient temperature

10: 97 percent / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 to -30 deg C, 1 h

With dmap; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; 9-borabicyclo[3.3.1]nonane dimer; cerium(III) chloride; water; dihydrogen peroxide; tert.-butyl lithium; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; Dess-Martin periodane; triethylamine; triphenylphosphine; sodium iodide; tin(ll) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/a805268i

upstream raw materials:

ethynylmagnesium chloride

3-[6-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-3-methylene-hexyl]-2,2,4-trimethyl-cyclohex-3-enecarbaldehyde

ethyl 2-acetyl-3-methylbut-2-enoate

pent-1-yn-5-ol

Downstream raw materials:

1-(6-Iodo-1-methoxy-3-methylenehexyl)-5-(1-oxoprop-2-ynyl)-2,6,6-trimethylcyclohex-1-ene

1-(6-Hydroxy-1-methoxy-3-methylenehexyl)-5-(1-oxoprop-2-ynyl)-2,6,6-trimethylcyclohex-1-ene

1-{3-[6-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-3-methylene-hexyl]-2,2,4-trimethyl-cyclohex-3-enyl}-propynone