2-Cyclohexene-1-ethanol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-ethenyl-, (1S,4S)-

Base Information

Chemical Name:2-Cyclohexene-1-ethanol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-ethenyl-, (1S,4S)-
CAS No.:851388-39-1
Molecular Formula:C16H30O2Si
Molecular Weight:282.498
Hs Code.:

Synonyms:

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Chemical Property of 2-Cyclohexene-1-ethanol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-ethenyl-, (1S,4S)-

Chemical Property:

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Technology Process of 2-Cyclohexene-1-ethanol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-ethenyl-, (1S,4S)-

There total 16 articles about 2-Cyclohexene-1-ethanol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-ethenyl-, (1S,4S)- 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%

: 851388-38-0
C₃₂H₄₈O₂Si₂

: 851388-39-1
2-[(1S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-vinyl-cyclohex-2-enyl]-ethanol

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 6h;
DOI:10.1055/s-2005-862388

Reference yield:

: 851388-15-3
3-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-penta-2,4-dien-1-ol

: 851388-39-1
2-[(1S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-vinyl-cyclohex-2-enyl]-ethanol

Guidance literature:: Multi-step reaction with 14 steps

1.1: 84 percent / Hg(OAc)2 / 18 h / 50 °C

2.1: 88 percent / i-Bu₃Al / CH₂Cl₂ / 1 h / 20 °C

3.1: imidazole; 4-DMAP / CH₂Cl₂ / 0.25 h / 20 °C

4.1: TMSCl; EtOH / 0.33 h / 20 °C

5.1: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

6.1: 95 percent / benzene / 1.5 h / 80 °C

7.1: 95 percent / i-Bu₂AlH / tetrahydrofuran / 0.17 h / 20 °C

8.1: (+)-DIPT; (i-PrO)4Ti; TBHP / 4 Angstroem molecular sieves / CH₂Cl₂ / 10 h / -25 °C

9.1: I₂; Ph₃P; imidazole / benzene / 0.33 h / 20 °C

10.1: Zn; HOAc / 2 h / 50 °C

11.1: Cl₂Ru=CHPh(PCy₃)2 / CH₂Cl₂ / 48 h / 20 °C

11.2: hydrolysis

12.1: 91 percent / imidazole; 4-DMAP / CH₂Cl₂ / 0.67 h / 20 °C

13.1: 71 percent / n-Bu₄NF; HOAc / tetrahydrofuran / 6 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; chloro-trimethyl-silane; oxalyl dichloride; ethanol; L-(+)-diisopropyl tartrate; mercury(II) diacetate; tetrabutyl ammonium fluoride; iodine; triisobutylaluminum; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc; Grubbs catalyst first generation; 4 A molecular sieve; In tetrahydrofuran; dichloromethane; benzene; 2.1: reductive Claisen rearrangement / 5.1: Swern oxidation / 6.1: Wittig reaction / 8.1: Katsuki-Sharpless asymmetric epoxidation;
DOI:10.1055/s-2005-862388

Reference yield:

: 851388-17-5
3-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-3-vinyl-pent-4-en-1-ol

: 851388-39-1
2-[(1S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-vinyl-cyclohex-2-enyl]-ethanol

Guidance literature:: Multi-step reaction with 12 steps

1.1: imidazole; 4-DMAP / CH₂Cl₂ / 0.25 h / 20 °C

2.1: TMSCl; EtOH / 0.33 h / 20 °C

3.1: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 95 percent / benzene / 1.5 h / 80 °C

5.1: 95 percent / i-Bu₂AlH / tetrahydrofuran / 0.17 h / 20 °C

6.1: (+)-DIPT; (i-PrO)4Ti; TBHP / 4 Angstroem molecular sieves / CH₂Cl₂ / 10 h / -25 °C

7.1: I₂; Ph₃P; imidazole / benzene / 0.33 h / 20 °C

8.1: Zn; HOAc / 2 h / 50 °C

9.1: Cl₂Ru=CHPh(PCy₃)2 / CH₂Cl₂ / 48 h / 20 °C

9.2: hydrolysis

10.1: 91 percent / imidazole; 4-DMAP / CH₂Cl₂ / 0.67 h / 20 °C

11.1: 71 percent / n-Bu₄NF; HOAc / tetrahydrofuran / 6 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; chloro-trimethyl-silane; oxalyl dichloride; ethanol; L-(+)-diisopropyl tartrate; tetrabutyl ammonium fluoride; iodine; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc; Grubbs catalyst first generation; 4 A molecular sieve; In tetrahydrofuran; dichloromethane; benzene; 3.1: Swern oxidation / 4.1: Wittig reaction / 6.1: Katsuki-Sharpless asymmetric epoxidation;
DOI:10.1055/s-2005-862388