1β-acetoxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene

Base Information

• Chemical Name: 1β-acetoxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene
• CAS No.: 115522-57-1
• Molecular Formula: C₁₆H₁₉ClO₃
• Molecular Weight: 294.778
• Mol file: 115522-57-1.mol

Synonyms:

Chemical Property of 1β-acetoxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1β-acetoxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene

There total 4 articles about 1β-acetoxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene 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: 77.0%

lithium acetate (546-89-4) + 6-(benzyloxy)-1,3-cycloheptadiene (115522-58-2) → 1β-acetoxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene (115522-57-1,150338-86-6)

Guidance literature:

With p-benzoquinone; lithium chloride; palladium diacetate; In acetic acid;

DOI:10.1016/S0040-4039(00)95578-3

Reference yield: 63.0%

lithium acetate (546-89-4) + 6-(benzyloxy)-1,3-cycloheptadiene (115522-58-2) → 1β-acetoxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene (115522-57-1,150338-86-6) + Acetic acid (1R,2S,6S)-6-benzyloxy-2-chloro-cyclohept-3-enyl ester (132622-28-7)

Guidance literature:

With p-benzoquinone; lithium chloride; palladium diacetate; In acetic acid; for 36h; Yields of byproduct given;

DOI:10.1021/jo00008a037

Reference yield:

cyclohepta-3,5-dien-1-ol (1121-63-7) → 1β-acetoxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene (115522-57-1,150338-86-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / tetrahydrofuran / 15 h / 50 °C

2: 63 percent / LiCl, p-benzoquinone, glacial acetic acid / Pd(OAc)2 / acetic acid / 36 h

With sodium hydride; acetic acid; p-benzoquinone; lithium chloride; palladium diacetate; In tetrahydrofuran; acetic acid;

DOI:10.1021/jo00008a037

upstream raw materials:

lithium acetate

6-(benzyloxy)-1,3-cycloheptadiene

cyclohepta-3,5-dien-1-ol

benzyl bromide

Downstream raw materials:

1β-acetoxy-4α-(p-toluenesulfonamido)-6α-(benzyloxy)-2-cycloheptene

Acetic acid (1R,4S,6S)-6-benzyloxy-4-(toluene-4-sulfonylamino)-cyclohept-2-enyl ester

1β-hydroxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene

Refernces

• 1、 Baeckvall, J. E.,Renko, Z. D.,Bystroem, S. E.. "STEREOCONTROLLED SYNTHESIS OF TROPANOL DERIVATIVES VIA PALLADIUM-CATALYZED REACTIONS". . p. 4199 - 4202. Retrieved 2007/10/02.