(2Z,4E)-5-(4-Hydroxy-2,6,6-trimethylcyclohex-1-enyl)-3-methoxycarbonylpenta-2,4-dienal

Base Information

• Chemical Name: (2Z,4E)-5-(4-Hydroxy-2,6,6-trimethylcyclohex-1-enyl)-3-methoxycarbonylpenta-2,4-dienal
• CAS No.: 152187-13-8
• Molecular Formula: C₁₆H₂₂O₄
• Molecular Weight: 278.348
• Mol file: 152187-13-8.mol

Synonyms:

Chemical Property of (2Z,4E)-5-(4-Hydroxy-2,6,6-trimethylcyclohex-1-enyl)-3-methoxycarbonylpenta-2,4-dienal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2Z,4E)-5-(4-Hydroxy-2,6,6-trimethylcyclohex-1-enyl)-3-methoxycarbonylpenta-2,4-dienal

There total 10 articles about (2Z,4E)-5-(4-Hydroxy-2,6,6-trimethylcyclohex-1-enyl)-3-methoxycarbonylpenta-2,4-dienal 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:

(4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one (20548-02-1,55058-51-0,60686-81-9,60686-82-0,82977-53-5,90082-06-7,90129-05-8,99881-84-2,60046-50-6) → (2Z,4E)-5-(4-Hydroxy-2,6,6-trimethylcyclohex-1-enyl)-3-methoxycarbonylpenta-2,4-dienal (152187-13-8)

Guidance literature:

Multi-step reaction with 10 steps

1: Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / Ambient temperature

2: 1) iPr₂NLi / 1) THF, hexane, 1 h, -78 deg C, 2) THF, 5 h, 0 deg C

3: Et₃N / PdCl₂(Ph₃P)2 / dimethylformamide / 22 h / 75 °C

4: LiAlH₄ / diethyl ether / 0.5 h / 0 °C

5: pyridine / 16 h / Ambient temperature

6: Pd(Ph₃P)4 / tetrahydrofuran / 1 h / Ambient temperature

7: 1) iPr₂NLi / 1) THF, hexane, 30 min, -78 deg C, 2) 20 min, -78 deg C

8: 1) NaH / 1) DMF, 40 min, r.t., 2) a) 10 min, 0 deg C, b) 15 min, r.t.

9: Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

10: 1) OsO₄, NaIO₄, 2) Al₂O₃ / 1) dioxane, water, 3 h, r.t., 2) ether, r.t.

With pyridine; dmap; aluminum oxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

(4R,6R)-4-[(tert-butyldimethylsilyl)oxy]-2,2,6-trimethylcyclohexan-1-one (130583-95-8) → (2Z,4E)-5-(4-Hydroxy-2,6,6-trimethylcyclohex-1-enyl)-3-methoxycarbonylpenta-2,4-dienal (152187-13-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 1) iPr₂NLi / 1) THF, hexane, 1 h, -78 deg C, 2) THF, 5 h, 0 deg C

2: Et₃N / PdCl₂(Ph₃P)2 / dimethylformamide / 22 h / 75 °C

3: LiAlH₄ / diethyl ether / 0.5 h / 0 °C

4: pyridine / 16 h / Ambient temperature

5: Pd(Ph₃P)4 / tetrahydrofuran / 1 h / Ambient temperature

6: 1) iPr₂NLi / 1) THF, hexane, 30 min, -78 deg C, 2) 20 min, -78 deg C

7: 1) NaH / 1) DMF, 40 min, r.t., 2) a) 10 min, 0 deg C, b) 15 min, r.t.

8: Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

9: 1) OsO₄, NaIO₄, 2) Al₂O₃ / 1) dioxane, water, 3 h, r.t., 2) ether, r.t.

With pyridine; aluminum oxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

Reference yield:

(-)-3-<(R)-4-(t-Butyl)dimethylsilyloxy-2,6,6-trimethyl-1-cyclohexen-1-yl>propen-1-ol (83021-09-4) → (2Z,4E)-5-(4-Hydroxy-2,6,6-trimethylcyclohex-1-enyl)-3-methoxycarbonylpenta-2,4-dienal (152187-13-8)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / 16 h / Ambient temperature

2: Pd(Ph₃P)4 / tetrahydrofuran / 1 h / Ambient temperature

3: 1) iPr₂NLi / 1) THF, hexane, 30 min, -78 deg C, 2) 20 min, -78 deg C

4: 1) NaH / 1) DMF, 40 min, r.t., 2) a) 10 min, 0 deg C, b) 15 min, r.t.

5: Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

6: 1) OsO₄, NaIO₄, 2) Al₂O₃ / 1) dioxane, water, 3 h, r.t., 2) ether, r.t.

With pyridine; aluminum oxide; sodium periodate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; sodium hydride; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran;

upstream raw materials:

(4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one

(4R,6R)-4-[(tert-butyldimethylsilyl)oxy]-2,2,6-trimethylcyclohexan-1-one

(-)-3-<(R)-4-(t-Butyl)dimethylsilyloxy-2,6,6-trimethyl-1-cyclohexen-1-yl>propen-1-ol

Methyl (3R,E)-3-(4-tert-Butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl)prop-2-enoate