4-(Tert-butyl-dimethyl-silanyloxy)-but-2-ynoic acid methyl ester

Base Information

• Chemical Name: 4-(Tert-butyl-dimethyl-silanyloxy)-but-2-ynoic acid methyl ester
• CAS No.: 117968-51-1
• Molecular Formula: C11H20 O3 Si
• Molecular Weight: 228.363
• DSSTox Substance ID: DTXSID00455854
• Nikkaji Number: J1.539.483H
• Wikidata: Q82278007
• Mol file: 117968-51-1.mol

Synonyms:117968-51-1;4-(TERT-BUTYL-DIMETHYL-SILANYLOXY)-BUT-2-YNOIC ACID METHYL ESTER;Methyl 4-((tert-butyldimethylsilyl)oxy)but-2-ynoate;METHYL 4-TERT-BUTYLDIMETHYLSILYLOXY-2-BUTYNOATE;methyl 4-[tert-butyl(dimethyl)silyl]oxybut-2-ynoate;methyl 4-[(tert-butyldimethylsilyl)oxy]but-2-ynoate;methyl 4-(tert-butyldimethylsilyloxy)but-2-ynoate;DTXSID00455854;AB1516;MFCD06658479;4-(TERT-BUTYLDIMETHYLSILANYLOXY)-BUT-2-YNOIC ACID METHYL ESTER,;SB31038;AS-44597;CS-0205867;Methyl4-tert-butyldimethylsilyloxy-2-butynoate;EN300-7413553;A803854;Methyl4-((tert-butyldimethylsilyl)oxy)but-2-ynoate;Methyl 4-{[tert-butyl(dimethyl)silyl]oxy}but-2-ynoate;4-(tert-Butyl-dimethylsilanyloxy)but-2-ynoicacidmethylester;4-(tert-Butyldimethylsiloxy)-2-butynoic acid methyl ester;METHYL 4-{[TERT-BUTYL(DIMETHYL)SILYL]OXY}-2-BUTYNOATE;2-Butynoic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, methyl ester

Chemical Property of 4-(Tert-butyl-dimethyl-silanyloxy)-but-2-ynoic acid methyl ester

Chemical Property:

• Boiling Point: 252.7±23.0 °C(Predicted)
• PSA: 35.53000
• Density: 0.955±0.06 g/cm3(Predicted)
• LogP: 2.18460
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 228.11817103
• Heavy Atom Count: 15
• Complexity: 288

Purity/Quality:

98% ^*data from raw suppliers

Methyl4-tert-Butyldimethylsilyloxy-2-butynoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCC#CC(=O)OC

Technology Process of 4-(Tert-butyl-dimethyl-silanyloxy)-but-2-ynoic acid methyl ester

There total 2 articles about 4-(Tert-butyl-dimethyl-silanyloxy)-but-2-ynoic acid methyl ester 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: 89.0%

tert-Butyldimethyl(prop-2-ynyloxy)silane (76782-82-6) + methyl chloroformate (79-22-1) → methyl-1-(tert-butyldimethylsilyloxy)-4-butynoate (117968-51-1)

Guidance literature:

tert-Butyldimethyl(prop-2-ynyloxy)silane; With n-butyllithium; In tetrahydrofuran; hexane; at -40 ℃; for 0.5h; Inert atmosphere;

methyl chloroformate; In tetrahydrofuran; hexane; at -40 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c5cc00129c

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → methyl-1-(tert-butyldimethylsilyloxy)-4-butynoate (117968-51-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1H-imidazole / dichloromethane / 1 h / 0 °C

2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -40 °C / Inert atmosphere

2.2: 2 h / -40 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1039/c5cc00129c

Reference yield: 98.0%

(2R,3S,4Z,6R,7S)-2-allyl-6-benzyloxy-7-benzyloxymethyl-2,3,6,7-tetrahydrooxepin-3-ol (863222-50-8) + methyl-1-(tert-butyldimethylsilyloxy)-4-butynoate (117968-51-1) → methyl (2E,2'R,3'S,4'Z,6'R,7'S)-3-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-4-(tert-butyldimethylsilyloxy)-2-butenoate (863222-49-5)

Guidance literature:

With trimethylphosphane; In tetrahydrofuran; dichloromethane; at 24 ℃; for 0.5h;

DOI:10.1016/j.tet.2005.05.073

upstream raw materials:

tert-Butyldimethyl(prop-2-ynyloxy)silane

methyl chloroformate

tert-butyldimethylsilyl chloride

Downstream raw materials:

methyl (E)-3-benzyloxy-4-(tert-butyldimethylsilanyloxy)but-2-enoate

methyl (2E,2'S,3'R,5'Z,8'S,9'R)-3-{(8'-benzyloxy-9'-benzyloxymethyl-2'-vinyl-2',3',4',7',8',9'-hexahydrooxonin-3'-yl)oxy}-4-(tert-butyldimethylsilyloxy)-2-butenoate

methyl (2E,2'R,3'S,4'Z,6'R,7'S)-3-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-4-(tert-butyldimethylsilyloxy)-2-butenoate

methyl (E)-3-benzyloxy-4-oxobut-2-enoate

Refernces

• 1、 Abe, Hideki,Tango, Haruhito,Kobayashi, Toyoharu,Ito, Hisanaka. "Asymmetric total synthesis and revision of absolute configurations of azaphilone derivative felinone A". . p. 4296 - 4298. Retrieved 2017.
• 2、 Linstadt, Roscoe T. H.,Peterson, Carl A.,Lippincott, Daniel J.,Jette, Carina I.,Lipshutz, Bruce H.. "Stereoselective silylcupration of conjugated alkynes in water at room temperature". supporting information. p. 4159 - 4163. Retrieved 2014/05/06.