3-hydroxytetradec-1-en-5-one O-benzyl-oxime

Base Information

• Chemical Name: 3-hydroxytetradec-1-en-5-one O-benzyl-oxime
• CAS No.: 892859-45-9
• Molecular Formula: C₂₁H₃₃NO₂
• Molecular Weight: 331.499

Synonyms:3-hydroxytetradec-1-en-5-one O-benzyl-oxime

Chemical Property of 3-hydroxytetradec-1-en-5-one O-benzyl-oxime

Chemical Property:

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Technology Process of 3-hydroxytetradec-1-en-5-one O-benzyl-oxime

There total 1 articles about 3-hydroxytetradec-1-en-5-one O-benzyl-oxime 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:

methyl nonyl ketone (112-12-9) → 3-hydroxytetradec-1-en-5-one O-benzyl-oxime (892859-45-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 78 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 98 percent / pyridine / methanol / 1 h / Heating

With pyridine; n-butyllithium; diisopropylamine; In tetrahydrofuran; methanol; hexane;

DOI:10.1021/ol0606435

Reference yield:

3-hydroxytetradec-1-en-5-one O-benzyl-oxime (892859-45-9) → (2R,3S,5S)-1-Methyl-5-nonyl-2-(4-trifluoromethyl-benzyl)-pyrrolidin-3-ol

Guidance literature:

Multi-step reaction with 7 steps

1: LiAlH₄ / diethyl ether / 1 h / Heating

2: 46 percent / diethyl ether / 2 h

3: 91 percent / imidazole / dimethylformamide / 20 °C

4: 52 percent / NaOtBu / Pd(OAc)2; bis(2-diphenylphosphinophenyl) ether / toluene / 90 °C

5: formic acid / tetrahydrofuran / 60 °C

6: tetrahydrofuran; H₂O / 0 - 60 °C

7: 30.8 mg / K₂CO₃; TBAF / tetrahydrofuran / 0 - 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; formic acid; tetrabutyl ammonium fluoride; potassium carbonate; sodium t-butanolate; palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol0606435

Reference yield:

3-hydroxytetradec-1-en-5-one O-benzyl-oxime (892859-45-9) → (+/-)-(2S,3S,5R)-2-(4-methoxybenzyl)-3-(tert-butyldimethylsilyloxy)-5-nonylpyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: LiAlH₄ / diethyl ether / 1 h / Heating

2: 39 percent / diethyl ether / 2 h

3: 94 percent / imidazole / dimethylformamide / 24 h / 20 °C

4: 55 percent / NaOtBu / Pd(OAc)2; bis(2-diphenylphosphinophenyl) ether / toluene / 90 °C

With 1H-imidazole; lithium aluminium tetrahydride; sodium t-butanolate; palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether; In diethyl ether; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol0606435

upstream raw materials:

methyl nonyl ketone

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