(R,S)-(1l,5l,7x)-7-<(tert-butyldimethylsilyl)oxy>methylbicyclo<3.3.1>non-2-ene

Base Information

Chemical Name:(R,S)-(1l,5l,7x)-7-<(tert-butyldimethylsilyl)oxy>methylbicyclo<3.3.1>non-2-ene
CAS No.:123099-72-9
Molecular Formula:C₁₆H₃₀OSi
Molecular Weight:266.499
Hs Code.:

Synonyms:(R,S)-(1l,5l,7x)-7-<(tert-butyldimethylsilyl)oxy>methylbicyclo<3.3.1>non-2-ene

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Chemical Property of (R,S)-(1l,5l,7x)-7-<(tert-butyldimethylsilyl)oxy>methylbicyclo<3.3.1>non-2-ene

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Technology Process of (R,S)-(1l,5l,7x)-7-<(tert-butyldimethylsilyl)oxy>methylbicyclo<3.3.1>non-2-ene

There total 1 articles about (R,S)-(1l,5l,7x)-7-<(tert-butyldimethylsilyl)oxy>methylbicyclo<3.3.1>non-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:

: 876-53-9
1,3-dibromoadamantane

: 123099-72-9
(R,S)-(1l,5l,7x)-7-<(tert-butyldimethylsilyl)oxy>methylbicyclo<3.3.1>non-2-ene

Guidance literature:: Multi-step reaction with 5 steps

1: 83 percent / 1 M NaOH / dioxane / 16 h / 185 °C

2: 1.) BF₃*THF, 2.) 10percent NaOH, 30percent aq. H₂O₂ / 1.) RT, 90 min, 2.) a) RT, 20 min, b) 50 deg C, 15 min

3: 80 percent / imidazole, DMAP / dimethylformamide / 1.) RT, 5 h, 2.) 45 deg C, overnight

4: 100 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

5: 92 percent / t-BuOK / tetrahydrofuran / 2 h / Ambient temperature

With 1H-imidazole; dmap; sodium hydroxide; boron trifluoride-tetrahydrofuran complex; potassium tert-butylate; dihydrogen peroxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00006a042

Reference yield:

: 123099-72-9
(R,S)-(1l,5l,7x)-7-<(tert-butyldimethylsilyl)oxy>methylbicyclo<3.3.1>non-2-ene

: 132514-50-2
(R,S)-(1l,2u,5u,7u)-2-(benzoyloxy)-7-methyl-7-ethenylbicyclo<3.3.1>nonane

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / m-chloroperoxybenzoic acid, NaHCO₃ / CH₂Cl₂ / 1 h / Ambient temperature

2: 72 percent / lithium triethylborohydride / tetrahydrofuran / 4 h / 45 °C

3: 1.) n-BuLi / 1.) Et₂O, -5 deg C, 5 min, 2.) RT, 30 min

4: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 8 h / Ambient temperature

5: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) Et₃N / 1.) -78 deg C, 30 min, 2.) from -78 deg C to RT, 35 min

6: 1.) t-BuOK / 1.) THF, 2-methyl-2-propanol, RT, 5 min, 2.) RT, 35 min

7: 1.) n-BuLi / 1.) THF, hexane, RT, 2.) RT, 20 min

With n-butyllithium; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; lithium triethylborohydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00006a042

Reference yield:

: 123099-72-9
(R,S)-(1l,5l,7x)-7-<(tert-butyldimethylsilyl)oxy>methylbicyclo<3.3.1>non-2-ene

: 132514-47-7
(R,S)-(1l,2u,5u,7x)-2-(benzoyloxy)-7-(hydroxymethyl)bicyclo<3.3.1>nonane

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / m-chloroperoxybenzoic acid, NaHCO₃ / CH₂Cl₂ / 1 h / Ambient temperature

2: 72 percent / lithium triethylborohydride / tetrahydrofuran / 4 h / 45 °C

3: 1.) n-BuLi / 1.) Et₂O, -5 deg C, 5 min, 2.) RT, 30 min

4: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 8 h / Ambient temperature

With n-butyllithium; tetrabutyl ammonium fluoride; lithium triethylborohydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00006a042