ChemicalBook CAS DataBase List 1-ETHOXY-2-METHYLPROPANE

1-ETHOXY-2-METHYLPROPANE synthesis

12synthesis methods

Product Name:1-ETHOXY-2-METHYLPROPANE
CAS Number:627-02-1
Molecular formula:C6H14O
Molecular Weight:102.17

78-83-1 Synthesis

78-83-1
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Benzenesulfonimidic acid, N-(1,1-dimethylethyl)-4-nitro-, ethyl ester

1569262-64-1
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627-02-1
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Yield: 81 %Spectr.

Reaction Conditions:

with tetrafluoroboric acid dimethyl ether complex in tetrachloromethane for 0.25 h;

Steps:

NMR-Scale Ethylation of Alcohols; General Procedure
General procedure: Sulfonimidate 1 (30 mg, 0.105 mmol, 10 mol% excess) and alcohol (0.97 mmol) were dissolved in CCl₄ (0.5 mL) along with an internal quantitative standard of PhF (2.3 μL, 0.024 mmol, 25 mol% of alcohol) and added to an NMR tube. The alcohols studied were 2-methylpropan-1-ol, butan-2-ol, 2-methylpropan-2-ol, but-3-en-2-ol, and neopentyl alcohol. Spectra of each mixture were run before addition of HBF₄·OMe₂ (1.0 μL, 9.7 μmol, 10 mol% of the alcohol amount). The NMR tubes were capped and inverted several times before recording the progress of each reaction. Reactions were followed by observing the disappearance of the sulfonimidate 1 tert-butyl peak at δ = 1.38 (in CCl₄) and the appearance of the sulfonamide 2 tert-butyl peak at δ = 1.23. In each spectrum, a small singlet appeared at δ = 3.2, which corresponds to Me₂O from the catalyst. Reactions with aliphatic alcohols were complete in less than 15 min. Several molecular sieve pellets were added to each NMR tube to neutralize the catalyst after completion of the reaction. Each product was isolated, by pipetting the CCl₄ solution from the precipitated sulfonamide 2. The samples were squeezed with a large pipet bulb through a cotton-plugged Pasteur pipet containing silica gel (ca. 3 cm). Each was rinsed with additional CCl₄ (2 × 0.25 mL) into an NMR tube for analysis. Excellent yields of the ethyl ethers of each alcohol were observed. No evidence for molecular rearrangements was seen.

References:

Maricich, Tom J.;Allan, Matthew J.;Kislin, Brett S.;Chen, Andrea I-T.;Meng, Fan-Chun;Bradford, Christine;Kuan, Nai-Chia;Wood, Jeremy;Aisagbonhi, Omonigho;Poste, Alethea;Wride, Dustin;Kim, Sylvia;Santos, Therese;Fimbres, Michael;Choi, Dianne;Elia, Haydi;Kaladjian, Joseph;Abou-Zahr, Ali;Mejia, Arturo [Synthesis,2013,vol. 45,# 24,art. no. SS-2013-M0543-OP,p. 3361 - 3368]