cis-1-oxo-3a-hydroxy-7-methoxy-8b-methyl-2,3,3a,8b-tetrahydro-1H-cyclopentabenzofuran

Base Information

• Chemical Name: cis-1-oxo-3a-hydroxy-7-methoxy-8b-methyl-2,3,3a,8b-tetrahydro-1H-cyclopentabenzofuran
• CAS No.: 72229-59-5
• Molecular Formula: C₁₃H₁₄O₄
• Molecular Weight: 234.252

Synonyms:cis-1-oxo-3a-hydroxy-7-methoxy-8b-methyl-2,3,3a,8b-tetrahydro-1H-cyclopentabenzofuran

Chemical Property of cis-1-oxo-3a-hydroxy-7-methoxy-8b-methyl-2,3,3a,8b-tetrahydro-1H-cyclopentabenzofuran

Chemical Property:

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Technology Process of cis-1-oxo-3a-hydroxy-7-methoxy-8b-methyl-2,3,3a,8b-tetrahydro-1H-cyclopentabenzofuran

There total 1 articles about cis-1-oxo-3a-hydroxy-7-methoxy-8b-methyl-2,3,3a,8b-tetrahydro-1H-cyclopentabenzofuran 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: 56.0%

1,2-bis(trimethylsiloxy)cyclobutene (17082-61-0) + 2'-acetoxy-5'-methoxyacetophenone (72229-47-1) → 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one (705-15-7) + 2-(β-carboxyethyl)-3-methyl-5-methoxybenzofuran (72229-70-0) + cis-1-oxo-3a-hydroxy-7-methoxy-8b-methyl-2,3,3a,8b-tetrahydro-1H-cyclopentabenzofuran (72229-59-5) + 2-methyl-2-(2-acetoxy-5-methoxyphenyl)cyclopentane-1,3-dione (72229-57-3)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; 1.) -40 deg C, 1 h, 2.) warmed to R_.T_. over 12 h.;

DOI:10.1021/jo01291a026

Reference yield:

cis-1-oxo-3a-hydroxy-7-methoxy-8b-methyl-2,3,3a,8b-tetrahydro-1H-cyclopentabenzofuran (72229-59-5) → 2-methyl-3α-acetoxy-2-(2-acetoxy-5-methoxyphenyl)cyclopentanone (72229-63-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / sodium cyanoborohydride / tetrahydrofuran / 2 h / Ambient temperature; at pH 3-4 ( 10 percent HCl).

2: 51 percent / pyridine / 4 h / Heating

With sodium cyanoborohydride; In tetrahydrofuran; pyridine;

DOI:10.1021/jo01291a026

Reference yield:

cis-1-oxo-3a-hydroxy-7-methoxy-8b-methyl-2,3,3a,8b-tetrahydro-1H-cyclopentabenzofuran (72229-59-5) → 5-bromo-2-methyl-3α-acetoxy-2-(2-acetoxy-5-methoxyphenyl)cyclopentanone (72229-64-2,72258-25-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / sodium cyanoborohydride / tetrahydrofuran / 2 h / Ambient temperature; at pH 3-4 ( 10 percent HCl).

2: 51 percent / pyridine / 4 h / Heating

3: 68 percent / cupric bromide / ethyl acetate; CHCl₃ / 2.5 h / Heating

With sodium cyanoborohydride; copper(ll) bromide; In tetrahydrofuran; pyridine; chloroform; ethyl acetate;

DOI:10.1021/jo01291a026

upstream raw materials:

1,2-bis(trimethylsiloxy)cyclobutene

2'-acetoxy-5'-methoxyacetophenone

Downstream raw materials:

2-methyl-3α-acetoxy-2-(2-acetoxy-5-methoxyphenyl)cyclopentanone

5-bromo-2-methyl-3α-acetoxy-2-(2-acetoxy-5-methoxyphenyl)cyclopentanone

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