methyl 2-{1-[3-(2-hydroxyethoxy)-4-(phenylmethoxy)butyl]indol-3-yl}-2-oxoacetate

Base Information

Chemical Name:methyl 2-{1-[3-(2-hydroxyethoxy)-4-(phenylmethoxy)butyl]indol-3-yl}-2-oxoacetate
CAS No.:336883-73-9
Molecular Formula:C₂₄H₂₇NO₆
Molecular Weight:425.481
Hs Code.:

Synonyms:methyl 2-{1-[3-(2-hydroxyethoxy)-4-(phenylmethoxy)butyl]indol-3-yl}-2-oxoacetate

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Chemical Property of methyl 2-{1-[3-(2-hydroxyethoxy)-4-(phenylmethoxy)butyl]indol-3-yl}-2-oxoacetate

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Technology Process of methyl 2-{1-[3-(2-hydroxyethoxy)-4-(phenylmethoxy)butyl]indol-3-yl}-2-oxoacetate

There total 6 articles about methyl 2-{1-[3-(2-hydroxyethoxy)-4-(phenylmethoxy)butyl]indol-3-yl}-2-oxoacetate 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%

: 79-37-8
oxalyl dichloride

: 124-41-4
sodium methylate

: 336883-72-8
2-{3-indolyl-1-[(phenylmethoxy)methyl]propoxy}ethan-1-ol

: 336883-73-9
methyl 2-{1-[3-(2-hydroxyethoxy)-4-(phenylmethoxy)butyl]indol-3-yl}-2-oxoacetate

Guidance literature:: oxalyl dichloride; 2-{3-indolyl-1-[(phenylmethoxy)methyl]propoxy}ethan-1-ol; In diethyl ether; at 0 ℃; for 0.5h;

sodium methylate; In methanol; diethyl ether; at -60 - 20 ℃; Further stages.;
DOI:10.1021/jo001605g

Reference yield:

: 120-72-9
indole

: 336883-73-9
methyl 2-{1-[3-(2-hydroxyethoxy)-4-(phenylmethoxy)butyl]indol-3-yl}-2-oxoacetate

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 1 h / 20 °C

1.2: 96 percent / dimethylformamide / 16 h / 20 °C

2.1: 91 percent / 1 N HCl / tetrahydrofuran / 20 °C

3.1: 82 percent / Bu₂SnO; CsF / dimethylformamide / 4 h / 20 °C

4.1: NaH / tetrahydrofuran / 1 h / 45 °C

4.2: 58 percent / tetrahydrofuran / 18 h / 45 °C

5.1: 97 percent / LiBH₄ / tetrahydrofuran; ethanol / 0 - 20 °C

6.1: diethyl ether / 0.5 h / 0 °C

6.2: 91 percent / diethyl ether; methanol / -60 - 20 °C

With hydrogenchloride; lithium borohydride; sodium hydride; di(n-butyl)tin oxide; cesium fluoride; In tetrahydrofuran; diethyl ether; ethanol; N,N-dimethyl-formamide;
DOI:10.1021/jo001605g

Reference yield:

: 336883-69-3
4-indolylbutane-1,2-diol

: 336883-73-9
methyl 2-{1-[3-(2-hydroxyethoxy)-4-(phenylmethoxy)butyl]indol-3-yl}-2-oxoacetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 82 percent / Bu₂SnO; CsF / dimethylformamide / 4 h / 20 °C

2.1: NaH / tetrahydrofuran / 1 h / 45 °C

2.2: 58 percent / tetrahydrofuran / 18 h / 45 °C

3.1: 97 percent / LiBH₄ / tetrahydrofuran; ethanol / 0 - 20 °C

4.1: diethyl ether / 0.5 h / 0 °C

4.2: 91 percent / diethyl ether; methanol / -60 - 20 °C

With lithium borohydride; sodium hydride; di(n-butyl)tin oxide; cesium fluoride; In tetrahydrofuran; diethyl ether; ethanol; N,N-dimethyl-formamide;
DOI:10.1021/jo001605g