(1′′RS)-6-(2,3,4-trimethoxy-6-(1-(prop-2-inyloxy)ethyl)phenyl)-2H-pyran-3(4H)-one

Base Information

Chemical Name:(1′′RS)-6-(2,3,4-trimethoxy-6-(1-(prop-2-inyloxy)ethyl)phenyl)-2H-pyran-3(4H)-one
CAS No.:1403559-00-1
Molecular Formula:C₁₉H₂₂O₆
Molecular Weight:346.38
Hs Code.:

Synonyms:(1′′RS)-6-(2,3,4-trimethoxy-6-(1-(prop-2-inyloxy)ethyl)phenyl)-2H-pyran-3(4H)-one

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Chemical Property of (1′′RS)-6-(2,3,4-trimethoxy-6-(1-(prop-2-inyloxy)ethyl)phenyl)-2H-pyran-3(4H)-one

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Technology Process of (1′′RS)-6-(2,3,4-trimethoxy-6-(1-(prop-2-inyloxy)ethyl)phenyl)-2H-pyran-3(4H)-one

There total 8 articles about (1′′RS)-6-(2,3,4-trimethoxy-6-(1-(prop-2-inyloxy)ethyl)phenyl)-2H-pyran-3(4H)-one 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: 41.0%

: 1403558-95-1
(1′′RS)-5-diazo-1-(2,3,4-trimethoxy-6-(1-(prop-2-ynyloxy)ethyl)phenyl)pentan-1,4-dione

: 1403559-00-1
(1′′RS)-6-(2,3,4-trimethoxy-6-(1-(prop-2-inyloxy)ethyl)phenyl)-2H-pyran-3(4H)-one

: 6-oxa-5-methyl-1,2,3-trimethoxy-9,12a-epoxy-5,7,9,11,12,12ahexahydrobenzo[a]heptalen-10-one

Guidance literature:: With dirhodium tetraacetate; In toluene; at 120 ℃; for 4.5h; Inert atmosphere; Reflux;
DOI:10.1002/ejoc.201200677

Reference yield:

: 1136-86-3
methyl (3,4,5-trimethoxyphenyl) ketone

: 1403559-00-1
(1′′RS)-6-(2,3,4-trimethoxy-6-(1-(prop-2-inyloxy)ethyl)phenyl)-2H-pyran-3(4H)-one

: 6-oxa-5-methyl-1,2,3-trimethoxy-9,12a-epoxy-5,7,9,11,12,12ahexahydrobenzo[a]heptalen-10-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: iodine; silver trifluoroacetate / chloroform / 5 h / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 16 h / Inert atmosphere; Reflux

3.1: sodium tetrahydroborate / ethanol / 4 h / 20 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

4.2: 2 h / 0 - 20 °C / Inert atmosphere

5.1: hydrogenchloride / tetrahydrofuran; water / 0.5 h / 20 °C / Inert atmosphere

5.2: 0.75 h / 0 - 20 °C / Inert atmosphere

6.1: triethylamine / tetrahydrofuran; diethyl ether / 1 h / -20 °C / Inert atmosphere

7.1: tetrahydrofuran; diethyl ether / -10 - 20 °C / Inert atmosphere

8.1: dirhodium tetraacetate / toluene / 4.5 h / 120 °C / Inert atmosphere; Reflux

With hydrogenchloride; dirhodium tetraacetate; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; iodine; silver trifluoroacetate; sodium hydride; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; chloroform; water; N,N-dimethyl-formamide; toluene; 2.1: |Stille Cross Coupling;
DOI:10.1002/ejoc.201200677

Reference yield:

: 1-(2-iodo-3,4,5-trimethoxyphenyl)ethanone

: 1403559-00-1
(1′′RS)-6-(2,3,4-trimethoxy-6-(1-(prop-2-inyloxy)ethyl)phenyl)-2H-pyran-3(4H)-one

: 6-oxa-5-methyl-1,2,3-trimethoxy-9,12a-epoxy-5,7,9,11,12,12ahexahydrobenzo[a]heptalen-10-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 16 h / Inert atmosphere; Reflux

2.1: sodium tetrahydroborate / ethanol / 4 h / 20 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

3.2: 2 h / 0 - 20 °C / Inert atmosphere

4.1: hydrogenchloride / tetrahydrofuran; water / 0.5 h / 20 °C / Inert atmosphere

4.2: 0.75 h / 0 - 20 °C / Inert atmosphere

5.1: triethylamine / tetrahydrofuran; diethyl ether / 1 h / -20 °C / Inert atmosphere

6.1: tetrahydrofuran; diethyl ether / -10 - 20 °C / Inert atmosphere

7.1: dirhodium tetraacetate / toluene / 4.5 h / 120 °C / Inert atmosphere; Reflux

With hydrogenchloride; dirhodium tetraacetate; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; water; N,N-dimethyl-formamide; toluene; 1.1: |Stille Cross Coupling;
DOI:10.1002/ejoc.201200677