1-(benzoyloxy)-5-methylideneheptan-6-one

Base Information

• Chemical Name: 1-(benzoyloxy)-5-methylideneheptan-6-one
• CAS No.: 187410-90-8
• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.306
• Mol file: 187410-90-8.mol

Synonyms:

Chemical Property of 1-(benzoyloxy)-5-methylideneheptan-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(benzoyloxy)-5-methylideneheptan-6-one

There total 1 articles about 1-(benzoyloxy)-5-methylideneheptan-6-one 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:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4-iodobutylbenzoate (19097-44-0) + acetylacetone (123-54-6,81235-32-7) → 1-(benzoyloxy)-5-methylideneheptan-6-one (187410-90-8)

Guidance literature:

With potassium carbonate; Yield given. Multistep reaction; 1) DMSO, RT, 10 h, 2) 3 h;

DOI:10.1021/jo970042e

Reference yield:

1-(benzoyloxy)-5-methylideneheptan-6-one (187410-90-8) → (3aβ,4α,8α)-4-(2-methyl-1,3-dioxolan-2-yl)-8a-(phenylselenyl)octahydro-4,8-methanoazulen-1-one

Guidance literature:

Multi-step reaction with 9 steps

1: 1) trimethyl orthoformate, p-toluenesulfonic acid, 2) aq. KOH / 1) RT, 10 h 2) 3 h

2: 88 percent / SO₃, pyridine / triethylamine; dimethylsulfoxide / 0.33 h

3: 87 percent / diethylamine / methanol / 5 h / Ambient temperature

4: CH₂Cl₂ / 8 h / 4 °C

5: dipotassium azodicarboxylate, glacial acetic acid / CH₂Cl₂ / 4 h

6: 1) KOH, 2) aq. K₃Fe(CN)6 / 1) EtOH, reflux, 2.5 h

7: acetonitrile / Heating

8: 2) KOH / 1) C₆H₆, 3 h, 2) EtOH, RT, 5 min

9: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2 h 20 min, 2.) -78 deg C to rt, rt, 2 h

With pyridine; potassium hydroxide; oxalyl dichloride; sulfur trioxide; potassium diazodicarboxylate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; diethylamine; triethylamine; potassium hexacyanoferrate(III); trimethyl orthoformate; In methanol; dichloromethane; dimethyl sulfoxide; triethylamine; acetonitrile;

DOI:10.1021/jo970042e

Reference yield:

1-(benzoyloxy)-5-methylideneheptan-6-one (187410-90-8) → (1α,5α,7α)-5-[(tert-butyldiphenylsilyl)oxy]-1-(2-methyl-1,3-dioxolan-2-yl)bicyclo[5.3.1]undecane-2,6-dione

Guidance literature:

Multi-step reaction with 13 steps

1: 1) trimethyl orthoformate, p-toluenesulfonic acid, 2) aq. KOH / 1) RT, 10 h 2) 3 h

2: 88 percent / SO₃, pyridine / triethylamine; dimethylsulfoxide / 0.33 h

3: 87 percent / diethylamine / methanol / 5 h / Ambient temperature

4: CH₂Cl₂ / 8 h / 4 °C

5: dipotassium azodicarboxylate, glacial acetic acid / CH₂Cl₂ / 4 h

6: 1) KOH, 2) aq. K₃Fe(CN)6 / 1) EtOH, reflux, 2.5 h

7: acetonitrile / Heating

8: 2) KOH / 1) C₆H₆, 3 h, 2) EtOH, RT, 5 min

9: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2 h 20 min, 2.) -78 deg C to rt, rt, 2 h

10: 1.) m-CPBA, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CCl₄, reflux, 8 h

11: DIBAL-H / CH₂Cl₂; hexane / 0.25 h / -78 °C

12: DMAP, NEt₃ / CH₂Cl₂ / 0 deg C to rt, 8 h

13: 70 percent / 1.) O₃, 2.) Me₂S / CH₂Cl₂; methanol / -78 deg C, 20 min, -78 deg C to rt, rt, 3 h

With pyridine; dmap; potassium hydroxide; oxalyl dichloride; dimethylsulfide; sulfur trioxide; potassium diazodicarboxylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; acetic acid; dimethyl sulfoxide; diethylamine; triethylamine; 3-chloro-benzenecarboperoxoic acid; potassium hexacyanoferrate(III); trimethyl orthoformate; In methanol; hexane; dichloromethane; dimethyl sulfoxide; triethylamine; acetonitrile;

DOI:10.1021/jo970042e

upstream raw materials:

formaldehyd

4-iodobutylbenzoate

acetylacetone

Downstream raw materials:

7-[5-(2-Methyl-[1,3]dioxolan-2-yl)-hex-5-enylidene]-2,3-diaza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid diethyl ester