(1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-(methoxymethoxy)-3-methylcyclohex-2-en-1-yl formate

Base Information

• Chemical Name: (1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-(methoxymethoxy)-3-methylcyclohex-2-en-1-yl formate
• CAS No.: 1432620-45-5
• Molecular Formula: C₁₃H₁₉ClO₄
• Molecular Weight: 274.744
• Mol file: 1432620-45-5.mol

Synonyms:(1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-(methoxymethoxy)-3-methylcyclohex-2-en-1-yl formate

Chemical Property of (1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-(methoxymethoxy)-3-methylcyclohex-2-en-1-yl formate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-(methoxymethoxy)-3-methylcyclohex-2-en-1-yl formate

There total 4 articles about (1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-(methoxymethoxy)-3-methylcyclohex-2-en-1-yl formate 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: 95.0%

(1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-hydroxy-3-methylcyclohex-2-en-1-yl formate (1376709-27-1) + chloromethyl methyl ether (107-30-2) → (1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-(methoxymethoxy)-3-methylcyclohex-2-en-1-yl formate (1432620-45-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene; at 20 ℃; for 12h;

DOI:10.1039/c3ob40120k

Reference yield:

(1R,6R)-6-(3-chloroprop-1-en-2-yl)-3-methyl-4-oxocyclohex-2-en-1-yl formate (1376709-10-2) → (1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-(methoxymethoxy)-3-methylcyclohex-2-en-1-yl formate (1432620-45-5)

Guidance literature:

Multi-step reaction with 2 steps

1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol

2: N-ethyl-N,N-diisopropylamine / dichloromethane; toluene / 12 h / 20 °C

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; toluene; 1: |Luche Cerium Reduction;

DOI:10.1039/c3ob40120k

Reference yield:

(4S,5R)-5-(3-chloroprop-1-en-2-yl)-4-hydroxy-2-methylcyclohex-2-enone (1376709-08-8) → (1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-(methoxymethoxy)-3-methylcyclohex-2-en-1-yl formate (1432620-45-5)

Guidance literature:

Multi-step reaction with 3 steps

1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran

2: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol

3: N-ethyl-N,N-diisopropylamine / dichloromethane; toluene / 12 h / 20 °C

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: |Mitsunobu Displacement / 2: |Luche Cerium Reduction;

DOI:10.1039/c3ob40120k

upstream raw materials:

(4S,5R)-4-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

(4S,5R)-5-(3-chloroprop-1-en-2-yl)-4-hydroxy-2-methylcyclohex-2-enone

(1R,6R)-6-(3-chloroprop-1-en-2-yl)-3-methyl-4-oxocyclohex-2-en-1-yl formate

(1R,4R,6R)-6-(3-chloroprop-1-en-2-yl)-4-hydroxy-3-methylcyclohex-2-en-1-yl formate

Downstream raw materials:

(1R,4R,6R)-6-(3-iodoprop-1-en-2-yl)-4-(methoxymethoxy)-3-methylcyclohex-2-en-1-yl formate