(5R)-1(R)-(2,2,2-trichloroethoxy)-4(R),6-dimethyl-2-oxabicyclo<3.3.1>non-2-ene

Base Information

• Chemical Name: (5R)-1(R)-(2,2,2-trichloroethoxy)-4(R),6-dimethyl-2-oxabicyclo<3.3.1>non-2-ene
• CAS No.: 112321-16-1
• Molecular Formula: C₁₇H₂₂O₂
• Molecular Weight: 258.36
• Mol file: 112321-16-1.mol

Synonyms:(5R)-1(R)-(2,2,2-trichloroethoxy)-4(R),6-dimethyl-2-oxabicyclo<3.3.1>non-2-ene

Chemical Property of (5R)-1(R)-(2,2,2-trichloroethoxy)-4(R),6-dimethyl-2-oxabicyclo<3.3.1>non-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R)-1(R)-(2,2,2-trichloroethoxy)-4(R),6-dimethyl-2-oxabicyclo<3.3.1>non-2-ene

There total 18 articles about (5R)-1(R)-(2,2,2-trichloroethoxy)-4(R),6-dimethyl-2-oxabicyclo<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: 59.0%

4-methyl-5(R)-<1-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2(R)-propyl>-3-cyclohexen-1-one (112321-13-8) + benzyl alcohol (100-51-6,185532-71-2) → (5R)-1(R)-(2,2,2-trichloroethoxy)-4(R),6-dimethyl-2-oxabicyclo<3.3.1>non-2-ene (112321-16-1)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; for 22h; Heating;

DOI:10.1021/jo00238a030

Reference yield:

2-((1R,5S)-5-Isopropenyl-2-methyl-cyclohex-2-enyl)-propan-1-ol (112321-00-3,112419-70-2) → (5R)-1(R)-(2,2,2-trichloroethoxy)-4(R),6-dimethyl-2-oxabicyclo<3.3.1>non-2-ene (112321-16-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / N-bromosuccinimide / acetone / 0.25 h / 0 °C

2: O₃ / CH₂Cl₂ / 0.2 h / -78 °C

3: acetic anhydride, Et₃N, (N,N-dimethylamino)pyridine / CH₂Cl₂ / 16 h / 40 °C

4: 7 percent / zinc / ethanol; H₂O / 16 h / Heating

5: 83 percent / Et₃N, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

6: 1.) oxalyl chloride, DMSO, Et₃N / 1.) CH₂Cl₂, -50 deg C, 15 min, 2.) a) -50 deg C, 5 min, b.) RT

7: 59 percent / pyridinium p-toluenesulfonate (PPTS) / CH₂Cl₂ / 22 h / Heating

With dmap; N-Bromosuccinimide; oxalyl dichloride; pyridinium p-toluenesulfonate; acetic anhydride; ozone; dimethyl sulfoxide; triethylamine; zinc; In ethanol; dichloromethane; water; acetone;

DOI:10.1021/jo00238a030

Reference yield:

1-((3R,3aR,5R,7S,7aS)-7-Bromo-3,7a-dimethyl-octahydro-benzofuran-5-yl)-1-methoxy-eth-1-yl-hydroperoxide (112347-68-9) → (5R)-1(R)-(2,2,2-trichloroethoxy)-4(R),6-dimethyl-2-oxabicyclo<3.3.1>non-2-ene (112321-16-1)

Guidance literature:

Multi-step reaction with 5 steps

1: acetic anhydride, Et₃N, (N,N-dimethylamino)pyridine / CH₂Cl₂ / 16 h / 40 °C

2: 7 percent / zinc / ethanol; H₂O / 16 h / Heating

3: 83 percent / Et₃N, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

4: 1.) oxalyl chloride, DMSO, Et₃N / 1.) CH₂Cl₂, -50 deg C, 15 min, 2.) a) -50 deg C, 5 min, b.) RT

5: 59 percent / pyridinium p-toluenesulfonate (PPTS) / CH₂Cl₂ / 22 h / Heating

With dmap; oxalyl dichloride; pyridinium p-toluenesulfonate; acetic anhydride; dimethyl sulfoxide; triethylamine; zinc; In ethanol; dichloromethane; water;

DOI:10.1021/jo00238a030

upstream raw materials:

4-methyl-5(R)-<1-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2(R)-propyl>-3-cyclohexen-1-one

benzyl alcohol

4-methyl-5(R)-<1-((2-tetrahydropyranyl)oxy)-2(R)-propyl>-3-cyclohexen-1(S)-one

(3R,3aR,5R,7S,7aS)-2,3,3a,4,5,5,7,7a-octahydro-7-bromo-3,7a-dimethyl-5-(2-propenyl)-1-oxainden-2-one