(+/-)-(Z)-7-<(tert-Butyldiphenylsilyl)oxy>-5-methyl-1-phenyl-1-heptene

Base Information

• Chemical Name: (+/-)-(Z)-7-<(tert-Butyldiphenylsilyl)oxy>-5-methyl-1-phenyl-1-heptene
• CAS No.: 149777-46-8
• Molecular Formula: C₃₀H₃₈OSi
• Molecular Weight: 442.717
• Mol file: 149777-46-8.mol

Synonyms:(+/-)-(Z)-7-<(tert-Butyldiphenylsilyl)oxy>-5-methyl-1-phenyl-1-heptene

Chemical Property of (+/-)-(Z)-7-<(tert-Butyldiphenylsilyl)oxy>-5-methyl-1-phenyl-1-heptene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-(Z)-7-<(tert-Butyldiphenylsilyl)oxy>-5-methyl-1-phenyl-1-heptene

There total 8 articles about (+/-)-(Z)-7-<(tert-Butyldiphenylsilyl)oxy>-5-methyl-1-phenyl-1-heptene 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:

Citronellol (106-22-9) → (+/-)-(Z)-7-<(tert-Butyldiphenylsilyl)oxy>-5-methyl-1-phenyl-1-heptene (149777-46-8)

Guidance literature:

Multi-step reaction with 7 steps

1: imidazole,, DMAP / CH₂Cl₂ / 5 h / Ambient temperature

2: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 12 min, 2.) room temp., 8 h

3: LiAlH₄ / diethyl ether / 8 h

4: Et₃N / diethyl ether / 1 h / Ambient temperature

5: NaI / acetone / 8 h / Ambient temperature

6: 89 percent / 20 h / 70 °C

7: 1.) KN(TMS)2, HMPA / 1.) THF, room temp., 20 min; -78 deg C, 10 min, 2.) -78 deg C to room temp., 1 h; room temp., 1 h

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; dimethylsulfide; potassium hexamethylsilazane; ozone; triethylamine; sodium iodide; In diethyl ether; dichloromethane; acetone;

DOI:10.1021/jo00071a024

Reference yield:

citronellol t-butyldiphenylsilyl ether (131883-94-8) → (+/-)-(Z)-7-<(tert-Butyldiphenylsilyl)oxy>-5-methyl-1-phenyl-1-heptene (149777-46-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 12 min, 2.) room temp., 8 h

2: LiAlH₄ / diethyl ether / 8 h

3: Et₃N / diethyl ether / 1 h / Ambient temperature

4: NaI / acetone / 8 h / Ambient temperature

5: 89 percent / 20 h / 70 °C

6: 1.) KN(TMS)2, HMPA / 1.) THF, room temp., 20 min; -78 deg C, 10 min, 2.) -78 deg C to room temp., 1 h; room temp., 1 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; dimethylsulfide; potassium hexamethylsilazane; ozone; triethylamine; sodium iodide; In diethyl ether; acetone;

DOI:10.1021/jo00071a024

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (+/-)-(Z)-7-<(tert-Butyldiphenylsilyl)oxy>-5-methyl-1-phenyl-1-heptene (149777-46-8)

Guidance literature:

Multi-step reaction with 7 steps

1: imidazole,, DMAP / CH₂Cl₂ / 5 h / Ambient temperature

2: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 12 min, 2.) room temp., 8 h

3: LiAlH₄ / diethyl ether / 8 h

4: Et₃N / diethyl ether / 1 h / Ambient temperature

5: NaI / acetone / 8 h / Ambient temperature

6: 89 percent / 20 h / 70 °C

7: 1.) KN(TMS)2, HMPA / 1.) THF, room temp., 20 min; -78 deg C, 10 min, 2.) -78 deg C to room temp., 1 h; room temp., 1 h

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; dimethylsulfide; potassium hexamethylsilazane; ozone; triethylamine; sodium iodide; In diethyl ether; dichloromethane; acetone;

DOI:10.1021/jo00071a024

upstream raw materials:

benzaldehyde

Citronellol

citronellol t-butyldiphenylsilyl ether

tert-butylchlorodiphenylsilane

Downstream raw materials:

(+/-)-(E)-3-Methyl-7-phenyl-6-heptenal

(+/-)-(Z)-3-Methyl-7-phenyl-6-heptenal

(Z)-3-Methyl-7-phenyl-6-hepten-1-ol