tert-butyl (2E)-3-{6-[3-(acetoxy)propyl]-2-[(5-bromo-2H-1,3-benzodioxol-4-yl)methoxy]-3-methoxyphenyl}prop-2-enoate

Base Information

Chemical Name:tert-butyl (2E)-3-{6-[3-(acetoxy)propyl]-2-[(5-bromo-2H-1,3-benzodioxol-4-yl)methoxy]-3-methoxyphenyl}prop-2-enoate
CAS No.:1620754-40-6
Molecular Formula:C₂₇H₃₁BrO₈
Molecular Weight:563.442
Hs Code.:

Synonyms:tert-butyl (2E)-3-{6-[3-(acetoxy)propyl]-2-[(5-bromo-2H-1,3-benzodioxol-4-yl)methoxy]-3-methoxyphenyl}prop-2-enoate

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Chemical Property of tert-butyl (2E)-3-{6-[3-(acetoxy)propyl]-2-[(5-bromo-2H-1,3-benzodioxol-4-yl)methoxy]-3-methoxyphenyl}prop-2-enoate

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Technology Process of tert-butyl (2E)-3-{6-[3-(acetoxy)propyl]-2-[(5-bromo-2H-1,3-benzodioxol-4-yl)methoxy]-3-methoxyphenyl}prop-2-enoate

There total 8 articles about tert-butyl (2E)-3-{6-[3-(acetoxy)propyl]-2-[(5-bromo-2H-1,3-benzodioxol-4-yl)methoxy]-3-methoxyphenyl}prop-2-enoate 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%

: 1620754-29-1
tert-butyl (2E)-3-{2-[(5-bromo-2H-1,3-benzodioxol-4-yl)methoxy]-6-(3-bromopropyl)-3-methoxyphenyl}prop-2-enoate

: 127-08-2
potassium acetate

: 1620754-40-6
tert-butyl (2E)-3-{6-[3-(acetoxy)propyl]-2-[(5-bromo-2H-1,3-benzodioxol-4-yl)methoxy]-3-methoxyphenyl}prop-2-enoate

Guidance literature:: With 18-crown-6 ether; In acetonitrile; at 80 ℃; Sealed tube;
DOI:10.1002/ejoc.201402218

Reference yield:

: 72744-54-8
5-bromo-benzo[1,3]dioxole-4-carbaldehyde

: 1620754-40-6
tert-butyl (2E)-3-{6-[3-(acetoxy)propyl]-2-[(5-bromo-2H-1,3-benzodioxol-4-yl)methoxy]-3-methoxyphenyl}prop-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1: sodium tetrahydroborate / tetrahydrofuran / 1.5 h / Reflux

2: chloro-trimethyl-silane; sodium iodide / acetonitrile / 1 h / 20 °C

3: potassium carbonate / acetone / 2 h / Reflux

4: palladium diacetate; triphenylphosphine; caesium carbonate; norborn-2-ene / acetonitrile / 16 h / 90 °C / Inert atmosphere; Sealed tube

5: 18-crown-6 ether / acetonitrile / 80 °C / Sealed tube

With norborn-2-ene; sodium tetrahydroborate; chloro-trimethyl-silane; 18-crown-6 ether; palladium diacetate; potassium carbonate; caesium carbonate; triphenylphosphine; sodium iodide; In tetrahydrofuran; acetone; acetonitrile; 3: |Williamson Ether Synthesis;
DOI:10.1002/ejoc.201402218

Reference yield:

: 2635-13-4
1,2-(methylenedioxy)-4-bromobenzene

: 1620754-40-6
tert-butyl (2E)-3-{6-[3-(acetoxy)propyl]-2-[(5-bromo-2H-1,3-benzodioxol-4-yl)methoxy]-3-methoxyphenyl}prop-2-enoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: -78 - 20 °C

2.1: sodium tetrahydroborate / tetrahydrofuran / 1.5 h / Reflux

3.1: chloro-trimethyl-silane; sodium iodide / acetonitrile / 1 h / 20 °C

4.1: potassium carbonate / acetone / 2 h / Reflux

5.1: palladium diacetate; triphenylphosphine; caesium carbonate; norborn-2-ene / acetonitrile / 16 h / 90 °C / Inert atmosphere; Sealed tube

6.1: 18-crown-6 ether / acetonitrile / 80 °C / Sealed tube

With norborn-2-ene; sodium tetrahydroborate; n-butyllithium; chloro-trimethyl-silane; 18-crown-6 ether; palladium diacetate; potassium carbonate; caesium carbonate; diisopropylamine; triphenylphosphine; sodium iodide; In tetrahydrofuran; hexane; acetone; acetonitrile; 4.1: |Williamson Ether Synthesis;
DOI:10.1002/ejoc.201402218