163667-14-9

Basic information

• Product Name: Benzeneacetaldehyde, a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-
• CAS NO: 163667-14-9
• Molecular Formula: C14H22O2Si
• Molecular Weight: 250.413
• Mol File: 163667-14-9.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: Benzeneacetaldehyde, a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetaldehyde, a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-(163667-14-9)
• EPA Substance Registry System: Benzeneacetaldehyde, a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-(163667-14-9)

Safety Data

• Hazardous Substances Data: 163667-14-9(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 611-71-2 MANDELIC ACID 
• 121618-58-4 trans-tert-butyldimethyl(((2S,3S)-3-phenyloxiran-2-yl)methoxy)silane 
• 56522-24-8 tert-butyldimethylsilyl cyanide 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 4358-87-6 (RS)-methyl mandelate 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 5849-19-4 <1,3>dithian-2-yl-phenyl-methanol 
• 568597-19-3 tert-butyl-([1,3]dithian-2-yl-phenyl-methoxy)-dimethyl-silane 
• 135348-18-4 (tert-Butyl-dimethyl-silanyloxy)-phenyl-acetic acid ethyl ester 
• 73795-12-7 1-phenylprop-2-en-1-yl tert-butyldimethylsilyl ether 
• 148204-86-8 (tert-butyldimethylsilanyloxy)phenylacetic acid methyl ester 
• 99808-99-8 (R,S)-α-[(tert-butyldimethylsilyl)oxy]-α-(phenyl)acetonitrile 

Downstream Products

• 306961-72-8 Benzyl-[2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-eth-(E)-ylidene]-amine 
• 103548-04-5 2-(tert-butyldimethylsilanyloxy)-1-phenylethan-1-one 
• 1003279-96-6 tert-butyl (RS,E)-4-(tert-butyldimethylsilyloxy)-4-phenylbut-2-enoate 
• 1260146-96-0 C₂₂H₂₆O₂Si 
• 1260146-34-6 1-hydroxy-1,4-diphenylbut-3-yne-2-one 
• 1260146-54-0 1-hydroxy-1,4-diphenylbut-3-yne-2-one 
• 127388-13-0 1,4-diphenyl-3-butyne-1,2-dione 
• 495-71-6 phenacylacetophenone 
• 176100-46-2 1-(naphthalen-2-yl)-4-phenylbutane-1,4-dione 
• 6938-44-9 ethyl 2-methyl-4-oxo-4-phenyl-butanoate 

Relevant articles and documents

The influence of α-coordinating groups of aldehydes on E/Z-selectivity and the use of quaternary ammonium counter ions for enhanced E-selectivity in the Julia–Kocienski reaction

Modified reaction conditions for improved E-selectivity of olefins in the Julia–Kocienski reaction of aldehydes having α-coordinating substituents are demonstrated. The chelating groups in aldehydes are expected to stabilize the syn-transition state with metal ions, whereas the weakly coordinating quaternary ammonium ions are devoid of all possible chelating interactions to enhance E-selectivity. A systematic investigation is presented to study the size of the neighbouring protecting groups of aldehydes and their chelation effect on E/Z-selectivity in the Julia–Kocienski reaction.

Synthesis of Highly Substituted Furans by a Cascade of Formal anti-Carbopalladation/Hydroxylation and Elimination

Highly substituted furans are generated by a cascade of formal anti-carbopalladation, attack of a nucleophilic hydroxy group, and aromatization by elimination of the emerging dihydrofuran derivative. Mono-, di-, and trisubstituted furans were obtained in good to excellent yields. When we attempted to access tetrasubstituted furan derivatives, an additional rearrangement was observed that resulted in the formation of chromenes. Follow-up chemistry shows the utility of TMS as a protecting group for the alkyne moiety.

β-fluoroamphetamines via the stereoselective synthesis of benzylic fluorides

A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF3-OEt 2 in CH2Cl2 at -20 -°C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective SN1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted β-fluoroamphetamines.