tert-butyl {3-hydroxymethyl-5-[3-(trimethylsilyl)prop-2-yn-1-yl]phenyl}carbamate

Base Information

Chemical Name:tert-butyl {3-hydroxymethyl-5-[3-(trimethylsilyl)prop-2-yn-1-yl]phenyl}carbamate
CAS No.:1639866-76-4
Molecular Formula:C₁₈H₂₇NO₃Si
Molecular Weight:333.503
Hs Code.:

Synonyms:tert-butyl {3-hydroxymethyl-5-[3-(trimethylsilyl)prop-2-yn-1-yl]phenyl}carbamate

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Chemical Property of tert-butyl {3-hydroxymethyl-5-[3-(trimethylsilyl)prop-2-yn-1-yl]phenyl}carbamate

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Technology Process of tert-butyl {3-hydroxymethyl-5-[3-(trimethylsilyl)prop-2-yn-1-yl]phenyl}carbamate

There total 5 articles about tert-butyl {3-hydroxymethyl-5-[3-(trimethylsilyl)prop-2-yn-1-yl]phenyl}carbamate 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: 71.0%

: 1639866-75-3
methyl 3-[(tert-butoxycarbonyl)amino]-5-(3-(trimethylsilyl)prop-2-yn-1-yl)benzoate

: 1639866-76-4
tert-butyl {3-hydroxymethyl-5-[3-(trimethylsilyl)prop-2-yn-1-yl]phenyl}carbamate

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -55 - 20 ℃; for 22h;
DOI:10.3762/bjoc.10.49

Reference yield:

: 220286-47-5
3-Amino-5-hydroxymethylbenzoic acid methyl ester

: 1639866-76-4
tert-butyl {3-hydroxymethyl-5-[3-(trimethylsilyl)prop-2-yn-1-yl]phenyl}carbamate

Guidance literature:: Multi-step reaction with 4 steps

1.1: ethanol / 20 h / 30 °C

2.1: triphenylphosphine; 1H-imidazole; bromine / dichloromethane / 2.5 h / 0 - 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / -7 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

3.3: 20 h / 65 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / dichloromethane; hexane / 22 h / -55 - 20 °C

With 1H-imidazole; n-butyllithium; bromine; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; ethanol; hexane; dichloromethane;
DOI:10.3762/bjoc.10.49

Reference yield:

: 1639866-73-1
C₁₄H₁₉NO₅

: 1639866-76-4
tert-butyl {3-hydroxymethyl-5-[3-(trimethylsilyl)prop-2-yn-1-yl]phenyl}carbamate

Guidance literature:: Multi-step reaction with 3 steps

1.1: triphenylphosphine; 1H-imidazole; bromine / dichloromethane / 2.5 h / 0 - 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / -7 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

2.3: 20 h / 65 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane; hexane / 22 h / -55 - 20 °C

With 1H-imidazole; n-butyllithium; bromine; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.3762/bjoc.10.49