927810-76-2

Usage

Uses

Used in Chemical Research and Synthesis:
Ethyl 4-Chlorobutyrate-d6 is used as a reagent for the preparation of labelled cyclopropane derivatives. Its deuterated nature allows for the tracking and analysis of chemical reactions and processes, making it a valuable tool in the study of reaction mechanisms and the development of new synthetic pathways.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Ethyl 4-Chlorobutyrate-d6 can be utilized as a starting material or intermediate in the synthesis of deuterated drug molecules. The incorporation of deuterium atoms can provide insights into the metabolic pathways and pharmacokinetics of these drugs, potentially leading to the optimization of drug efficacy and safety.
Used in Analytical Chemistry:
Ethyl 4-Chlorobutyrate-d6 can also be employed in analytical chemistry as an internal standard or a reference compound in various analytical techniques such as mass spectrometry, nuclear magnetic resonance (NMR) spectroscopy, and infrared (IR) spectroscopy. Its deuterated properties can enhance the accuracy and precision of these analytical methods, particularly in the study of complex mixtures and the identification of unknown compounds.

Upstream product

• 64-17-5 ethanol 
• 77568-65-1 <2H6>γ-Butyrolactone 

Downstream Products

• 927810-77-3 ethyl 2,2,3,3-tetradeuteriocyclopropanecarboxylate 

Relevant academic research and scientific papers

Stereoselective preparation of six diastereomeric quatercyclopropanes from bicyclopropylidene and some derivatives

Diastereomeric meso- and d,l-bis(bicyclopropylidenyl) (5) were obtained upon oxidation with oxygen of a higher-order cuprate generated from lithiobicyclopropylidene (4) in 50 and 31 % yield, respectively. Their perdeuterated analogues meso-[D14]- and d,l-[D14]-5 were obtained along the same route from perdeuterated bicyclopropylidene [D 8]-3 (synthesized in six steps in 7.4% overall yield from [D8]-THF) in 20.5% yield each. Dehalogenative coupling of 1,1-dibromo-2- cyclopropylcyclopropane (6) gave a mixture of all possible stereoisomers of 1,5-dicyclopropylbicyclopropylidene 16 in 69% yield, from which (Z)-cis-16 was separated by preparative gas chromatography (26% yield). The crystal structure of meso-5 looks like a super-position of the crystal structures of two outer bicyclopropylidene units (3) and one inner s-rrans-bicyclopropyl unit, whereas the two outer cyclopropyl moieties adopt a gauche orientation with respect to the cyclopropane rings at the inner bicyclopropylidene units in (Z)-cis-16. Birch reduction with lithium in liquid ammonia of meso-5 and d,l-5 gave two pairs of diastereomeric quatercyclopropanes trans,trans-(R*,S*, R*, S*)-17/cis,trans-(R*,S*,R*,R*)-18 and trans,trans-(R*,S*,S*,R*)-19/cis,trans-(R*, S*,S*,S*)-20 in 97 and 76% yield, respectively, in a ratio 9:1 for every pair. The latter diastereomer was also obtained as the sole product by Birch reduction of (Z)-cis-16 in 96% yield. Under the same conditions, tetradecadeuterio analogues trans,trans-[D14]-(R*S*, R*,S*)-17/cis,trans-[D14]-(R*, S*,R*, R*)-18 (8:1) and trans,trans[D14]-(R*,S*,S*, R*)-19/cis,trans-[D14](R*,S*,S*,S*)-20 (12:1) were prepared from mwo-[D14]-5 and d,l-[D14]-5 in 37 and 63 % yield, respectively. Reduction of meso-5 with diimine gave the cis,cisquatercyclopropane (S*,S*,R*,R*)-21 as the main product (58% yield) along with the cis,trans-diastereomer (S*,S*, R*,S*)-18 (29% yield). Thus, five of the six possible diastereomeric quatercyclopropanes were obtained from meso-5, d,l-5, and (Z)-cis-16. The X-ray crystal structure analyses of transjrans-(R*,S*,R*,S*)- 17 and cis,cis(S*,S*,R*,R*)-21 revealed for the both an unusual conformation in which the central bicyclopropyl unit adopts an s-fran.s-(antiperiplanar) orientation with φ=180.0°, and the two terminal bicyclopropyl moieties adopt a synclinal conformation with φ = 49.8 and 72.0°, respectively. In solution the vicinal coupling constants 〈3JH,H〉 in trans,trans(R*,R*, R*,S*)-[D14]-17, trans,trans(R*,S*,S*, R*)-[D14]-19, trans,trans(R*,S*,R*,R*)- [D14]-18 and trans,cis(R*,S*,S*,S*)-[D 14]-20 were found to be 4.1, 4.7, 5.9 and 5.9 Hz, respectively. This indicates a predominance of the all-gauche conformer in (R*,S*, R*,S*)-17 and a decreasing fraction of it in this sequence of the other diastereomers.