3-[(E)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-hex-2-enyl]-2-hydroxy-4-methoxy-6-methoxymethoxymethyl-5-methyl-benzoic acid

Base Information

Chemical Name:3-[(E)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-hex-2-enyl]-2-hydroxy-4-methoxy-6-methoxymethoxymethyl-5-methyl-benzoic acid
CAS No.:100045-87-2
Molecular Formula:C₂₅H₄₂O₇Si
Molecular Weight:482.69
Hs Code.:

Synonyms:3-[(E)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-hex-2-enyl]-2-hydroxy-4-methoxy-6-methoxymethoxymethyl-5-methyl-benzoic acid

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Chemical Property of 3-[(E)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-hex-2-enyl]-2-hydroxy-4-methoxy-6-methoxymethoxymethyl-5-methyl-benzoic acid

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Technology Process of 3-[(E)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-hex-2-enyl]-2-hydroxy-4-methoxy-6-methoxymethoxymethyl-5-methyl-benzoic acid

There total 7 articles about 3-[(E)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-hex-2-enyl]-2-hydroxy-4-methoxy-6-methoxymethoxymethyl-5-methyl-benzoic acid 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:

: 35334-60-2
(E)-6-acetoxy-4-methyl-4-hexenal

: 100045-87-2
3-[(E)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-hex-2-enyl]-2-hydroxy-4-methoxy-6-methoxymethoxymethyl-5-methyl-benzoic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 84 percent / NaBH₄ / ethanol / 0.42 h / 25 °C

2: triethylamine / 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 h / Ambient temperature

3: K₂CO₃ / methanol / 24 h / Ambient temperature

4: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li₂CuCl₄ / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h

5: 73 percent / benzene / 14 h / 120 °C / in a sealed tube

6: 85 percent / Br₂, tert butylamine / toluene / 4 h / -78 - 5 °C

7: 1.) CH₃Li, LiBr, 2.) tert-BuLi / 1.) diethyl ether, 50 min, 2.) diethyl ether/pentane, -78 deg C, 1 h, 3.) -78 to 0 deg C, 30 min

With sodium tetrahydroborate; n-butyllithium; dilithium tetrachlorocuprate; methyllithium; bromine; tert.-butyl lithium; potassium carbonate; methanesulfonyl chloride; tert-butylamine; triethylamine; lithium bromide; dmap; In methanol; ethanol; dichloromethane; toluene; benzene;
DOI:10.1021/ja00264a038

Reference yield:

: 100045-79-2
<(2E)-6-Hydroxy-3-methyl-2-hexenyl>acetat

: 100045-87-2
3-[(E)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-hex-2-enyl]-2-hydroxy-4-methoxy-6-methoxymethoxymethyl-5-methyl-benzoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: triethylamine / 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 h / Ambient temperature

2: K₂CO₃ / methanol / 24 h / Ambient temperature

3: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li₂CuCl₄ / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h

4: 73 percent / benzene / 14 h / 120 °C / in a sealed tube

5: 85 percent / Br₂, tert butylamine / toluene / 4 h / -78 - 5 °C

6: 1.) CH₃Li, LiBr, 2.) tert-BuLi / 1.) diethyl ether, 50 min, 2.) diethyl ether/pentane, -78 deg C, 1 h, 3.) -78 to 0 deg C, 30 min

With n-butyllithium; dilithium tetrachlorocuprate; methyllithium; bromine; tert.-butyl lithium; potassium carbonate; methanesulfonyl chloride; tert-butylamine; triethylamine; lithium bromide; dmap; In methanol; dichloromethane; toluene; benzene;
DOI:10.1021/ja00264a038

Reference yield:

: 100045-80-5
(E)-6-((tert-butyldimethylsilyl)oxy)-3-methylhex-2-en-1-yl acetate

: 100045-87-2
3-[(E)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-hex-2-enyl]-2-hydroxy-4-methoxy-6-methoxymethoxymethyl-5-methyl-benzoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: K₂CO₃ / methanol / 24 h / Ambient temperature

2: 1.) n-BuLi, 2.) methanesulfonyl chloride, 3.) Li₂CuCl₄ / 1.) THF/n-hexane, -78 deg C, 35 min, 2.) -78 deg C, 2 h, 3.) THF/n-hexane/diethyl ether -78 deg C to room temp. over 2.5 h then 25 deg C, 3 h

3: 73 percent / benzene / 14 h / 120 °C / in a sealed tube

4: 85 percent / Br₂, tert butylamine / toluene / 4 h / -78 - 5 °C

5: 1.) CH₃Li, LiBr, 2.) tert-BuLi / 1.) diethyl ether, 50 min, 2.) diethyl ether/pentane, -78 deg C, 1 h, 3.) -78 to 0 deg C, 30 min

With n-butyllithium; dilithium tetrachlorocuprate; methyllithium; bromine; tert.-butyl lithium; potassium carbonate; methanesulfonyl chloride; tert-butylamine; lithium bromide; In methanol; toluene; benzene;
DOI:10.1021/ja00264a038