DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL

Base Information

• Chemical Name: DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL
• CAS No.: 31469-15-5
• Molecular Formula: C8H18O2Si
• Molecular Weight: 174.315
• Hs Code.: 29319090
• Mol file: 31469-15-5.mol

Synonyms:Silane,[(1-methoxy-2-methyl-1-propenyl)oxy]trimethyl- (9CI);Silane,[(1-methoxy-2-methylpropenyl)oxy]trimethyl- (8CI);1-Methoxy-1-(trimethylsiloxy)-2-methyl-1-propene;1-Methoxy-1-(trimethylsiloxy)-2-methylpropene;1-Methoxy-1-(trimethylsilyloxy)-2-methyl-1-propene;1-Methoxy-1-(trimethylsilyloxy)-2-methylpropene;1-Methoxy-2,2-dimethyl-1-(trimethylsiloxy)ethene;1-Methoxy-2-methyl-1-(trimethylsiloxy)-1-propene;1-Methoxy-2-methyl-1-(trimethylsiloxy)propene;1-Methoxy-2-methyl-1-(trimethylsilyloxy)propene;1-Methoxy-2-methyl-1-trimethylsilyloxy-1-propene;Dimethylketene methyltrimethylsilyl acetal;Methyl trimethylsilyl dimethylketene acetal;O-Methyl-O-(trimethylsilyl)dimethylketene acetal;[(1-Methoxy-2-methyl-1-propenyl)oxy]trimethylsilane;[(1-Methoxy-2-methylpropenyl)oxy]trimethylsilane;

Chemical Property of DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL

Chemical Property:

• Vapor Pressure: 8.76mmHg at 25°C
• Refractive Index: n20/D 1.415(lit.)
• Boiling Point: 137.4 °C at 760mmHg
• Flash Point: 14.4 °C
• PSA: 18.46000
• Density: 0.858 g/cm³
• LogP: 2.73570
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: freely sol organic solvents.
• Water Solubility.: Hydrolyzes in water.

Purity/Quality:

98% ^*data from raw suppliers

(1-Methoxy-2-methylprop-1-enoxy)trimethylsilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Physical properties: bp 35 °C/15 mmHg; d 0.858 g cm?3.
• Uses: 1-Methoxy-2-methyl-1-(trimethylsilyloxy) propene is widely used as functional equivalent of enolate of methyl isobutyrate; ester enolate surrogate in electrophilic reactions including alkylation, aldol reaction, Michael reaction, initiator for group transfer polymerization of acrylates, nitroarylation, oxidation, dimerization, and cycloadditions. 1-Methoxy-2-methyl-1-(trimethylsiloxy)propene is used in the synthesis of chiral β-lactams by reacting with (S)-alkylidene(1-arylethyl)amines in the presence of titanium tetrachloride. It acts as a catalyst or initiator in the group-transfer polymerization. It is also used as a versatile reagent in conjugate addition4 and aldol reactions.

Technology Process of DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL

There total 9 articles about DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL 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: 98.0%

chloro-trimethyl-silane (75-77-4) + Methyl isobutyrate (547-63-7,133320-07-7,67505-84-4) → 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene (31469-15-5)

Guidance literature:

Methyl isobutyrate; With lithium diisopropyl amide; In tetrahydrofuran; at -20 ℃; for 2h; Inert atmosphere;

chloro-trimethyl-silane; In tetrahydrofuran; at -20 - 20 ℃; Reagent/catalyst;

Reference yield: 95.0%

trimethylsilan (993-07-7) + methacrylic acid methyl ester (80-62-6,114512-63-9,143476-91-9,25188-98-1,9011-14-7) + acetone (67-64-1) → 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene (31469-15-5) + 3-trimethylsiloxy-2,2,3-trimethylbutyrate (115579-81-2)

Guidance literature:

rhodium(III) chloride; Ambient temperature;

DOI:10.1016/S0040-4039(00)96631-0

Reference yield: 85.0%

trimethylsilan (993-07-7) + methacrylic acid methyl ester (80-62-6,114512-63-9,143476-91-9,25188-98-1,9011-14-7) → 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene (31469-15-5)

Guidance literature:

With 2,6-di-tert-butyl-4-methyl-phenol; rhodium(III) chloride; In tetrahydrofuran; at 40 - 50 ℃; other methacrylates;

DOI:10.1021/jo00296a080

upstream raw materials:

chloro-trimethyl-silane

Methyl isobutyrate

dimethyl dimethylmalonate

2-bromo-2-methylpropionic acid methyl ester

Downstream raw materials:

2-(1-Adamantyl)-2-methylpropionsaeure-methylester

methyl 3-hydroxy-2,2-dimethyl-3-phenylpropanoate

methyl 3-hydroxy-3-(4-methoxyphenyl)-2,2-dimethylpropionate

methyl 2-methyl-2-(2-oxocyclohexyl)propionate

Refernces

• 1、 Zhou, Fengtao,Yamamoto, Hisashi. "A Disulfonimide Catalyst for Highly Enantioselective Mukaiyama-Mannich Reaction". . p. 4974 - 4977. Retrieved 2016.
• 2、 -. "Preparation method of fexofenadine". Paragraph 0051; 0067-0069. . Retrieved 2021/04/17.
• 3、 Balcells, Sandra,Haughey, Maxwell B.,Walker, Johannes C. L.,Josa-Culleré, Laia,Towers, Christopher,Donohoe, Timothy J.. "Asymmetric Total Synthesis of (-)-(3 R)-Inthomycin C". supporting information. p. 3583 - 3586. Retrieved 2018/06/26.