acetic acid 5-[6-(2-hydroxy-ethyl)-3,6-dihydro-2H-pyran-2-yl]-4-methyl-2-methylene-pentyl ester

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Chemical Name:acetic acid 5-[6-(2-hydroxy-ethyl)-3,6-dihydro-2H-pyran-2-yl]-4-methyl-2-methylene-pentyl ester
CAS No.:362471-95-2
Molecular Formula:C₁₆H₂₆O₄
Molecular Weight:282.38
Hs Code.:

Synonyms:

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Chemical Property of acetic acid 5-[6-(2-hydroxy-ethyl)-3,6-dihydro-2H-pyran-2-yl]-4-methyl-2-methylene-pentyl ester

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Technology Process of acetic acid 5-[6-(2-hydroxy-ethyl)-3,6-dihydro-2H-pyran-2-yl]-4-methyl-2-methylene-pentyl ester

There total 29 articles about acetic acid 5-[6-(2-hydroxy-ethyl)-3,6-dihydro-2H-pyran-2-yl]-4-methyl-2-methylene-pentyl ester 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: 80.0%

: 362471-85-0
acetic acid 2-(3-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-allyl ester

: 362471-95-2
acetic acid 5-[6-(2-hydroxy-ethyl)-3,6-dihydro-2H-pyran-2-yl]-4-methyl-2-methylene-pentyl ester

Guidance literature:: With fluorosilicic acid; In acetonitrile;
DOI:10.1016/j.bmcl.2003.12.001

Reference yield:

: 5949-05-3
(S)-Citronellal

: 362471-95-2
acetic acid 5-[6-(2-hydroxy-ethyl)-3,6-dihydro-2H-pyran-2-yl]-4-methyl-2-methylene-pentyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: diethyl ether / -78 °C

1.2: 75 percent / aq. NaOH; H₂O₂

2.1: 65 percent / Pd(OAc)2; Et₃N / acetonitrile / 80 °C

3.1: 85 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 40 °C

4.1: LiClO₄ / diethyl ether / 0 °C

5.1: 50 percent / NaBH₄ / tetrahydrofuran; H₂O / 0 °C

6.1: mCPBA; aq. NaHCO₃ / CH₂Cl₂ / 0 °C

7.1: aq. H₂SO₄ / tetrahydrofuran

8.1: 70 percent / Et₃N; DMAP / 0 °C

9.1: 95 percent / Pb(OAc)4 / toluene

10.1: CH₂Cl₂

10.2: Et₃N

11.1: 55 percent / NaBH₄; CeCl₃ / methanol / -78 °C

12.1: 95 percent / DMAP; pyridine

13.1: 80 percent / H₂SiF₆ / acetonitrile

With pyridine; lead(IV) acetate; dmap; palladium diacetate; sodium tetrahydroborate; Grubbs catalyst first generation; fluorosilicic acid; cerium(III) chloride; sulfuric acid; lithium perchlorate; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; acetonitrile;
DOI:10.1016/j.bmcl.2003.12.001

Reference yield:

: 362471-71-4
(2R,S)-2-[(2S)-2,6-dimethylhept-5-enyl]oxirane

: 362471-95-2
acetic acid 5-[6-(2-hydroxy-ethyl)-3,6-dihydro-2H-pyran-2-yl]-4-methyl-2-methylene-pentyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 41 percent / H₂O / Jacobsen (salen)Co(III)(OAc) / various solvent(s) / 36 h / 22 °C

2.1: 91 percent / nBuLi; BF₃-etherate / tetrahydrofuran / 2 h / -95 °C

3.1: quinoline; H₂ / Lindlar's catalyst / ethanol / 6 h / 22 °C

4.1: pTsOH / benzene / 1 h / Heating

5.1: mCPBA; NaHCO₃ / CH₂Cl₂ / 0.33 h / 0 °C

6.1: aq. HClO₄ / tetrahydrofuran / 1 h / 22 °C

7.1: aq. NaIO₄ / methanol / 3 h / 22 °C

8.1: NEt₃ / CH₂Cl₂ / 12 h / 22 °C

9.1: diethyl ether; CHCl₃ / 12 h / 22 °C

9.2: K₂CO₃ / CHCl₃ / 6 h / 22 °C

10.1: DIBAL / CH₂Cl₂ / 1 h / -78 °C

10.2: 78 percent / pTsOH / 1 h / 22 °C

11.1: 93 percent / DMAP; pyridine / 0.75 h / 22 °C

12.1: LiClO₄ / ethyl acetate; CH₂Cl₂ / 12 h / 22 °C

13.1: NaBH₄ / methanol / 0.5 h / 0 °C

With pyridine; quinoline; dmap; sodium tetrahydroborate; sodium periodate; n-butyllithium; perchloric acid; boron trifluoride diethyl etherate; water; hydrogen; lithium perchlorate; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; [(S,S)-N,N-bis-(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamino-Co(III)-acetate]; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; chloroform; ethyl acetate; benzene; 3.1: Lindlar hydrogenation / 8.1: Eschenmoser methylenation;
DOI:10.1055/s-2001-15145