4-<(tert-Butyldimethylsilyl)oxy>butyronitrile

Base Information

• Chemical Name: 4-<(tert-Butyldimethylsilyl)oxy>butyronitrile
• CAS No.: 123703-37-7
• Molecular Formula: C₁₀H₂₁NOSi
• Molecular Weight: 199.368
• Mol file: 123703-37-7.mol

Synonyms:4-<(tert-Butyldimethylsilyl)oxy>butyronitrile

Chemical Property of 4-<(tert-Butyldimethylsilyl)oxy>butyronitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-<(tert-Butyldimethylsilyl)oxy>butyronitrile

There total 1 articles about 4-<(tert-Butyldimethylsilyl)oxy>butyronitrile 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: 57.0%

4-(tert-butyldimethylsilanyloxy)butanal (87184-81-4) → 4-butanolide (96-48-0) + 4-hydroxy-1-butanitrile (628-22-8) + 4-<(tert-Butyldimethylsilyl)oxy>butyronitrile (123703-37-7)

Guidance literature:

With O-(diphenylphosphinyl)hydroxylamine; In toluene; at 20 - 85 ℃; chemoselective reaction;

DOI:10.1021/jo301133y DOI:10.1021/jo301133y

Reference yield:

4-<(tert-Butyldimethylsilyl)oxy>butyronitrile (123703-37-7) → 1-<12-(Carbo-tert-butoxyamino)-5,9-diaza-5,9-dicarbo-tert-butoxy-7-<1-<2-<(tert-butyldimetylsilyl)oxy>ethyl>>dodecanyl>-O-(2-tetrahydropyranyl)tyrosinamide

Guidance literature:

Multi-step reaction with 14 steps

1: 86 percent / LDA / tetrahydrofuran; cyclohexane / 1.) -78 deg C, 30 min, then 30 min, 2.) -78 deg C, 2 h

2: 66 percent / LiBH₄ / CH₂Cl₂ / 4 h / 23 °C

3: 67 percent / LAH / diethyl ether / 1.) 0 deg C, 1 h, 2.) r.t., 3.5 h

4: 83 percent / methanol / 24 h / 23 °C

5: 99 percent / CH₂Cl₂ / 3.75 h / 23 °C

6: 77 percent / LAH / diethyl ether / 1.5 h / 0 °C

7: 85 percent / CH₂Cl₂ / 0.83 h / 23 °C

8: 68 percent / N-chlorosuccinimide, dimethyl sulfide / toluene / 3.5 h / -25 - -20 °C

9: Na₂SO₄ / ethanol / 20.5 h / 23 °C

10: NaBH₄ / ethanol / 10 h / 23 °C

11: 88 percent / CH₂Cl₂ / 11.5 h / 23 °C

12: 95 percent / H₂ / 10percent Pd/C / methanol / 4.5 h / 23 °C / 760 Torr

13: 68 percent / methanol / 26 h / 23 °C

14: 90 percent / H₂ / Pd/C / methanol / 2 h / 23 °C / 760 Torr

With sodium tetrahydroborate; N-chloro-succinimide; lithium aluminium tetrahydride; lithium borohydride; dimethylsulfide; hydrogen; sodium sulfate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; cyclohexane; toluene;

DOI:10.1021/jo00076a017

Reference yield:

4-<(tert-Butyldimethylsilyl)oxy>butyronitrile (123703-37-7) → 1-<12-(Carbo-tert-butoxyamino)-5,9-diaza-5,9-dicarbo-tert-butoxy-7-<1-<2-<(tert-butyldimetylsilyl)oxy>ethyl>>dodecanyl>-N-butyryl-O-(2-tetrahydropyranyl)tyrosinamide

Guidance literature:

Multi-step reaction with 15 steps

1: 86 percent / LDA / tetrahydrofuran; cyclohexane / 1.) -78 deg C, 30 min, then 30 min, 2.) -78 deg C, 2 h

2: 66 percent / LiBH₄ / CH₂Cl₂ / 4 h / 23 °C

3: 67 percent / LAH / diethyl ether / 1.) 0 deg C, 1 h, 2.) r.t., 3.5 h

4: 83 percent / methanol / 24 h / 23 °C

5: 99 percent / CH₂Cl₂ / 3.75 h / 23 °C

6: 77 percent / LAH / diethyl ether / 1.5 h / 0 °C

7: 85 percent / CH₂Cl₂ / 0.83 h / 23 °C

8: 68 percent / N-chlorosuccinimide, dimethyl sulfide / toluene / 3.5 h / -25 - -20 °C

9: Na₂SO₄ / ethanol / 20.5 h / 23 °C

10: NaBH₄ / ethanol / 10 h / 23 °C

11: 88 percent / CH₂Cl₂ / 11.5 h / 23 °C

12: 95 percent / H₂ / 10percent Pd/C / methanol / 4.5 h / 23 °C / 760 Torr

13: 68 percent / methanol / 26 h / 23 °C

14: 90 percent / H₂ / Pd/C / methanol / 2 h / 23 °C / 760 Torr

15: 78 percent / Et₃N / CHCl₃ / 4 h / 23 °C

With sodium tetrahydroborate; N-chloro-succinimide; lithium aluminium tetrahydride; lithium borohydride; dimethylsulfide; hydrogen; sodium sulfate; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; chloroform; cyclohexane; toluene;

DOI:10.1021/jo00076a017

upstream raw materials:

4-(tert-butyldimethylsilanyloxy)butanal

Downstream raw materials:

1,5-di-tert-butyldimethylsilyloxy-2-phenyl-pentane-3-carbonitrile

1,5-di-tert-butyldimethylsilyloxy-1-phenyl-pentane-3-carbonitrile

[2-{[(E)-4-Benzyloxycarbonylamino-butylimino]-methyl}-4-(tert-butyl-dimethyl-silanyloxy)-butyl]-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester

7-<1-<2-<(tert-Butyldimethylsilyl)oxy>ethyl>>-N'''-carbobenzoxy-N,N',N''-tricarbo-tert-butoxythermospermine

Refernces

• 1、 Laulhe, Sebastien,Gori, Sadakatali S.,Nantz, Michael H.. "A chemoselective, one-pot transformation of aldehydes to nitriles". . p. 9334 - 9337,4. Retrieved 2012/12/12.