Bicyclo[2.2.1]hept-5-en-2-ol, 1,4,5,6-tetrachloro-7,7-dimethoxy-, acetate, endo-

Base Information

• Chemical Name: Bicyclo[2.2.1]hept-5-en-2-ol, 1,4,5,6-tetrachloro-7,7-dimethoxy-, acetate, endo-
• CAS No.: 64145-54-6
• Molecular Formula: C₁₁H₁₂Cl₄O₄
• Molecular Weight: 350.026
• Mol file: 64145-54-6.mol

Synonyms:

Chemical Property of Bicyclo[2.2.1]hept-5-en-2-ol, 1,4,5,6-tetrachloro-7,7-dimethoxy-, acetate, endo-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Bicyclo[2.2.1]hept-5-en-2-ol, 1,4,5,6-tetrachloro-7,7-dimethoxy-, acetate, endo-

There total 1 articles about Bicyclo[2.2.1]hept-5-en-2-ol, 1,4,5,6-tetrachloro-7,7-dimethoxy-, acetate, endo- 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: 91.0%

vinyl acetate (108-05-4,9003-20-7) + 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene (2207-27-4) → (+/-)-(1R,2S,4S)-1,4,5,6-tetrachloro-7,7-dimethoxybicyclo[2.2.1]hept-5-en-2-yl acetate (40001-91-0,64145-54-6,112460-48-7,133962-67-1)

Guidance literature:

for 108h; Heating;

DOI:10.1021/ja00211a031

Reference yield:

(+/-)-(1R,2S,4S)-1,4,5,6-tetrachloro-7,7-dimethoxybicyclo[2.2.1]hept-5-en-2-yl acetate (40001-91-0,64145-54-6,112460-48-7,133962-67-1) → (1R,4R,6R,8R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxy-6-(4-methoxy-phenoxymethoxymethyl)-2-oxa-tricyclo[6.4.0.04,12]dodec-11-en-7-one

Guidance literature:

Multi-step reaction with 20 steps

1.1: 100 percent / K₂CO₃ / methanol / 0.33 h

2.1: 88 percent / Na; NH₃ / methanol / 1 h

3.1: 98 percent / pyridine

4.1: 94 percent / AcOH; H₂O / 0.67 h / 150 °C

5.1: 73 percent / diethyl ether / 0 °C

6.1: 26 percent / SeO₂; t-BuOOH / 72 h / 20 °C

7.1: 80 percent / NaBH₄; CeCl₃*7H₂O

8.1: 69 percent / BnNEt₃Cl; NaOH / toluene; H₂O / 0.17 h

9.1: 93 percent / 2,6-lutidine

10.1: LiAlH₄ / tetrahydrofuran

11.1: Dess-Martin reagent

12.1: LDA; MoOPH / -23 °C

12.2: Dess-Martin reagent / CH₂Cl₂

13.1: 79 percent / LDA / tetrahydrofuran / -78 °C

14.1: 85 percent / SOCl₂; pyridine

15.1: 92 percent / (t-BuO)3AlHLi / tetrahydrofuran / 6 h / 20 °C

16.1: 89 percent / PrSLi; HMPA

17.1: 96 percent / 2-chloro-1-methylpyridinium iodide; Et₃N / CH₂Cl₂ / Heating

18.1: 99 percent / chlorobenzene / 3 h / 132 °C

19.1: 95 percent / DIBAL-H / CH₂Cl₂ / -78 °C

20.1: 90 percent / CF₃CO₂H / tetrahydrofuran; H₂O

With pyridine; 2,6-dimethylpyridine; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; selenium(IV) oxide; thionyl chloride; cerium(III) chloride; MoO₅*pyridine*HMPA; 2-chloro-1-methyl-pyridinium iodide; N-benzyl-N,N,N-triethylammonium chloride; ammonia; water; sodium; diisobutylaluminium hydride; lithium n-propylmercaptide; potassium carbonate; Dess-Martin periodane; acetic acid; lithium tri-t-butoxyaluminum hydride; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; chlorobenzene; toluene; 18.1: siloxy-Cope rearrangement;

DOI:10.1139/v03-086

Reference yield:

(+/-)-(1R,2S,4S)-1,4,5,6-tetrachloro-7,7-dimethoxybicyclo[2.2.1]hept-5-en-2-yl acetate (40001-91-0,64145-54-6,112460-48-7,133962-67-1) → (1R,3S,4R,6R,8R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-methoxy-6-(4-methoxy-phenoxymethoxymethyl)-2-oxa-tricyclo[6.4.0.04,12]dodec-11-en-7-one

Guidance literature:

Multi-step reaction with 21 steps

1.1: 100 percent / K₂CO₃ / methanol / 0.33 h

2.1: 88 percent / Na; NH₃ / methanol / 1 h

3.1: 98 percent / pyridine

4.1: 94 percent / AcOH; H₂O / 0.67 h / 150 °C

5.1: 73 percent / diethyl ether / 0 °C

6.1: 26 percent / SeO₂; t-BuOOH / 72 h / 20 °C

7.1: 80 percent / NaBH₄; CeCl₃*7H₂O

8.1: 69 percent / BnNEt₃Cl; NaOH / toluene; H₂O / 0.17 h

9.1: 93 percent / 2,6-lutidine

10.1: LiAlH₄ / tetrahydrofuran

11.1: Dess-Martin reagent

12.1: LDA; MoOPH / -23 °C

12.2: Dess-Martin reagent / CH₂Cl₂

13.1: 79 percent / LDA / tetrahydrofuran / -78 °C

14.1: 85 percent / SOCl₂; pyridine

15.1: 92 percent / (t-BuO)3AlHLi / tetrahydrofuran / 6 h / 20 °C

16.1: 89 percent / PrSLi; HMPA

17.1: 96 percent / 2-chloro-1-methylpyridinium iodide; Et₃N / CH₂Cl₂ / Heating

18.1: 99 percent / chlorobenzene / 3 h / 132 °C

19.1: 95 percent / DIBAL-H / CH₂Cl₂ / -78 °C

20.1: 90 percent / CF₃CO₂H / tetrahydrofuran; H₂O

21.1: 96 percent / TsOH*pyridine

With pyridine; 2,6-dimethylpyridine; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; selenium(IV) oxide; thionyl chloride; cerium(III) chloride; MoO₅*pyridine*HMPA; 2-chloro-1-methyl-pyridinium iodide; N-benzyl-N,N,N-triethylammonium chloride; ammonia; water; sodium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; lithium n-propylmercaptide; potassium carbonate; Dess-Martin periodane; acetic acid; lithium tri-t-butoxyaluminum hydride; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; chlorobenzene; toluene; 18.1: siloxy-Cope rearrangement;

DOI:10.1139/v03-086

upstream raw materials:

vinyl acetate

5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene