3-<2-(1α,6α-dimethyl-4α-t-butyldimethylsilyloxycyclohex-2-enyl)ethyl>but-2-en-4-olide

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Chemical Name:3-<2-(1α,6α-dimethyl-4α-t-butyldimethylsilyloxycyclohex-2-enyl)ethyl>but-2-en-4-olide
CAS No.:111724-23-3
Molecular Formula:C₂₀H₃₄O₃Si
Molecular Weight:350.574
Hs Code.:

Synonyms:

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Chemical Property of 3-<2-(1α,6α-dimethyl-4α-t-butyldimethylsilyloxycyclohex-2-enyl)ethyl>but-2-en-4-olide

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Technology Process of 3-<2-(1α,6α-dimethyl-4α-t-butyldimethylsilyloxycyclohex-2-enyl)ethyl>but-2-en-4-olide

There total 11 articles about 3-<2-(1α,6α-dimethyl-4α-t-butyldimethylsilyloxycyclohex-2-enyl)ethyl>but-2-en-4-olide 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: 85.0%

: 111724-22-2,111724-31-3
3-<1-phenylsulphonyl-2-(1α,6α-dimethyl-4α-t-butyldimethylsilyloxycyclohex-2-enyl)-ethyl>but-2-en-4-olide

: 111724-23-3,115395-49-8
3-<2-(1α,6α-dimethyl-4α-t-butyldimethylsilyloxycyclohex-2-enyl)ethyl>but-2-en-4-olide

Guidance literature:: With disodium hydrogenphosphate; sodium amalgam; In methanol; at -20 ℃; for 1.5h;
DOI:10.1016/S0040-4020(01)88114-X

Reference yield:

: 497-03-0
2-methylbut-2-enal

: 111724-23-3,115395-49-8
3-<2-(1α,6α-dimethyl-4α-t-butyldimethylsilyloxycyclohex-2-enyl)ethyl>but-2-en-4-olide

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) hydroquinone; 2.) 2N HCl / 1.) 140 deg C, 14-18 h.; 2.) THF, 30 min.

2: 66 percent / p-TSA / benzene / Heating

3: 67 percent / thallium (III) nitrate trihydrate / tetrahydrofuran; methanol / 0.08 h / 0 °C

4: 77 percent / NaBH₄ / ethanol / 0 °C

5: 89 percent / pyridine, DMAP / CH₂Cl₂ / 6 h / Ambient temperature

6: 75 percent / Tl(OCOCF₃)3 / tetrahydrofuran / 2 h / Ambient temperature

7: 92 percent / n-BuLi / tetrahydrofuran; hexane / -78 deg C, 5 min. then room temp.

8: 97 percent / LiHBEt₃ / tetrahydrofuran

9: 1.) n-BuLi, HMPA; 2.) TBAF / 1.) THF, hexane, -78 deg C, 15 min.; 2.) THF, 1 h.

10: 85 percent / Na₂HPO₄, 4percent Na/Hg / methanol / 1.5 h / -20 °C

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; tetrabutyl ammonium fluoride; lithium triethylborohydride; hydroquinone; thallium(III) nitrate; thallium(III) trifluoroacetate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; benzene;
DOI:10.1016/S0040-4020(01)88114-X

Reference yield:

: 80267-24-9,87927-54-6
4β-formyl-4α,5α-dimethylcyclohex-2-enone

: 111724-23-3,115395-49-8
3-<2-(1α,6α-dimethyl-4α-t-butyldimethylsilyloxycyclohex-2-enyl)ethyl>but-2-en-4-olide

Guidance literature:: Multi-step reaction with 9 steps

1: 66 percent / p-TSA / benzene / Heating

2: 67 percent / thallium (III) nitrate trihydrate / tetrahydrofuran; methanol / 0.08 h / 0 °C

3: 77 percent / NaBH₄ / ethanol / 0 °C

4: 89 percent / pyridine, DMAP / CH₂Cl₂ / 6 h / Ambient temperature

5: 75 percent / Tl(OCOCF₃)3 / tetrahydrofuran / 2 h / Ambient temperature

6: 92 percent / n-BuLi / tetrahydrofuran; hexane / -78 deg C, 5 min. then room temp.

7: 97 percent / LiHBEt₃ / tetrahydrofuran

8: 1.) n-BuLi, HMPA; 2.) TBAF / 1.) THF, hexane, -78 deg C, 15 min.; 2.) THF, 1 h.

9: 85 percent / Na₂HPO₄, 4percent Na/Hg / methanol / 1.5 h / -20 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; tetrabutyl ammonium fluoride; lithium triethylborohydride; thallium(III) nitrate; thallium(III) trifluoroacetate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; benzene;
DOI:10.1016/S0040-4020(01)88114-X