endo-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-1<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>hept-2-ene

Base Information

• Chemical Name: endo-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-1<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>hept-2-ene
• CAS No.: 142041-35-8
• Molecular Formula: C₂₁H₃₂O₃Si
• Molecular Weight: 360.569
• Mol file: 142041-35-8.mol

Synonyms:endo-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-1<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>hept-2-ene

Chemical Property of endo-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-1<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>hept-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of endo-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-1<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>hept-2-ene

There total 6 articles about endo-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-1<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>hept-2-ene 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: 96.0%

tert-butyldimethylsilyl chloride (18162-48-6) + endo-5-methyl-1-<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>hept-5-en-2-ol (142041-33-6) → endo-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-1<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>hept-2-ene (142041-35-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 16h; Ambient temperature;

DOI:10.1021/jo00042a036

Reference yield:

2-Benzyloxymethyl-4-methyl-furan-3-carboxylic acid (142041-30-3) → endo-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-1<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>hept-2-ene (142041-35-8)

Guidance literature:

Multi-step reaction with 5 steps

1: copper-bronze, quinoline / 1 h / Heating

2: 98 percent / hydroquinone / CH₂Cl₂ / 312 h / 9050090 Torr

3: 1) 1 M aq. KOH, 2) 37percent aq. formaldehyde / 1) THF, water, r.t., 45 min, 2) 20 min

4: 95 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 1.5 h / -78 °C

5: 96 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

With 1H-imidazole; quinoline; potassium hydroxide; formaldehyd; copper; diisobutylaluminium hydride; hydroquinone; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00042a036

Reference yield:

4-methyl-2-<(phenylmethoxy)methyl>furan (142041-31-4) → endo-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-1<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>hept-2-ene (142041-35-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / hydroquinone / CH₂Cl₂ / 312 h / 9050090 Torr

2: 1) 1 M aq. KOH, 2) 37percent aq. formaldehyde / 1) THF, water, r.t., 45 min, 2) 20 min

3: 95 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 1.5 h / -78 °C

4: 96 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

With 1H-imidazole; potassium hydroxide; formaldehyd; diisobutylaluminium hydride; hydroquinone; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00042a036

upstream raw materials:

tert-butyldimethylsilyl chloride

endo-5-methyl-1-<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>hept-5-en-2-ol

4-methyl-2-<(phenylmethoxy)methyl>furan

2-Benzyloxymethyl-4-methyl-furan-3-carboxylic acid

Downstream raw materials:

(2-exo,3-endo,6-endo)-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-1-<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>heptan-2-ol

(3-endo,6-endo)-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-1-<(phenylmethoxy)methyl>-7-oxabicyclo<2.2.1>heptan-2-one