1-{6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinolin-5-yl}but-3-en-1-ol

Base Information

Chemical Name:1-{6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinolin-5-yl}but-3-en-1-ol
CAS No.:430436-51-4
Molecular Formula:C₂₉H₄₁NO₃Si
Molecular Weight:479.735
Hs Code.:

Synonyms:1-{6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinolin-5-yl}but-3-en-1-ol

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Chemical Property of 1-{6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinolin-5-yl}but-3-en-1-ol

Chemical Property:

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Technology Process of 1-{6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinolin-5-yl}but-3-en-1-ol

There total 5 articles about 1-{6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinolin-5-yl}but-3-en-1-ol 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:

: 239071-11-5
6-[2-(tert-butyldimethylsilanoxy)-6-methyloxyphenyl]=2,2,4-trimethyl-1,2-dihydroquinoline-5-carbaldehyde

: 1730-25-2
allylmagnesium bromide

: 430436-51-4
1-{6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinolin-5-yl}but-3-en-1-ol

: 1-{6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroxyquinolin-3-yl}but-3-en-1-ol

Guidance literature:: allylmagnesium bromide; With B-chlorodiisopinocampheylborane; In diethyl ether; at -78 ℃; for 2h;

6-[2-(tert-butyldimethylsilanoxy)-6-methyloxyphenyl]=2,2,4-trimethyl-1,2-dihydroquinoline-5-carbaldehyde; In diethyl ether; at -77 ℃; Further stages. Title compound not separated from byproducts.;
DOI:10.1021/ja0171198

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 430436-51-4
1-{6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinolin-5-yl}but-3-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetrahydrofuran / 0 - 20 °C

1.2: tetrahydrofuran / 0.5 h / 40 °C

2.1: DIBAL / CH₂Cl₂; heptane / -45 - -40 °C

3.1: 4.8 g / 2-iodoxybenzoic acid / 1-methyl-pyrrolidin-2-one / 2 h / 20 °C

4.1: (+)-DIP-Cl / diethyl ether / 2 h / -78 °C

4.2: diethyl ether / -77 °C

With diisobutylaluminium hydride; B-chlorodiisopinocampheylborane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; n-heptane; dichloromethane;
DOI:10.1021/ja0171198

Reference yield:

: 239070-97-4
2,5-dihydro-10-methoxy-5-oxo-2,2,4-trimethyl-1H-[1]benzopyrano [3,4-f]quinoline

: 430436-51-4
1-{6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinolin-5-yl}but-3-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetrahydrofuran / 0 - 20 °C

1.2: tetrahydrofuran / 0.5 h / 40 °C

2.1: DIBAL / CH₂Cl₂; heptane / -45 - -40 °C

3.1: 4.8 g / 2-iodoxybenzoic acid / 1-methyl-pyrrolidin-2-one / 2 h / 20 °C

4.1: (+)-DIP-Cl / diethyl ether / 2 h / -78 °C

4.2: diethyl ether / -77 °C

With diisobutylaluminium hydride; B-chlorodiisopinocampheylborane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; n-heptane; dichloromethane;
DOI:10.1021/ja0171198