43749
Ethyl 1,3-dithiane-2-carboxylate
technical, ≥90% (GC)
Synonym(s):
Glyoxylic acid ethyl ester trimethylenemercaptal
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About This Item
Empirical Formula (Hill Notation):
C7H12O2S2
CAS Number:
Molecular Weight:
192.30
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
243-838-4
Beilstein/REAXYS Number:
1424352
MDL number:
Assay:
≥90% (GC)
InChI key
ANEDZEVDORCLPM-UHFFFAOYSA-N
InChI
1S/C7H12O2S2/c1-2-9-6(8)7-10-4-3-5-11-7/h7H,2-5H2,1H3
SMILES string
CCOC(=O)C1SCCCS1
grade
technical
assay
≥90% (GC)
refractive index
n20/D 1.539 (lit.), n20/D 1.541
bp
75-77 °C/0.2 mmHg (lit.)
density
1.22 g/mL at 25 °C (lit.)
functional group
ester, thioether
Quality Level
Related Categories
General description
Ethyl 1,3-dithiane-2-carboxylate is an α-keto acid equivalent and bulky equivalent of acetate. It participates in syn-selective aldol reactions. It can be prepared from the reaction of ethyl diethoxyacetate and 1,3-propanedithiol in the presence of BF3/Et2O. Asymmetric oxidation of ethyl 1,3-dithiane-2-carboxylate by Modena protocol has been reported to afford trans bis-sulfoxide in 60% yield. Carbanion from ethyl 1,3-dithiane-2-carboxylate may be employed for the preparation of α-keto esters.
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Alkylation of the carbanion from methyl bis (ethylthio) acetate with alkyl and aralkyl halides.
Lerner LM.
The Journal of Organic Chemistry, 41(12), 2228-2229 (1976)
Convenient synthesis of α-keto esters.
Eliel EL and Hartmann AA.
The Journal of Organic Chemistry, 37(3), 505-506 (1972)
Varinder K. Aggarwal et al.
The Journal of organic chemistry, 63(21), 7306-7310 (2001-10-24)
Asymmetric oxidation of a range of 1,3-dithianes was studied using the Kagan protocol [CHP (4 equiv), (+)-DET (2 equiv), Ti(OiPr)(4) (1 equiv), and H(2)O (1 equiv) at -35 degrees C for 48 h]. 1,3-Dithiane itself gave monoxide (30% ee) and
L.A. Flippin et al.
Tetrahedron Letters, 26, 2977-2977 (1985)
Phase Transfer Catalysis for Preparation and Alkylation of Ethyl 1,3-Dithiane-2-carboxylate.
Lissel M.
Synthetic Communications, 11(4), 343-346 (1981)
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