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| | ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE Basic information |
| | ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE Chemical Properties |
| Boiling point | 85 °C/0.1 mmHg (lit.) | | density | 1.249 g/mL at 25 °C (lit.) | | refractive index | n20/D 1.539(lit.) | | Fp | >230 °F | | storage temp. | 2-8°C | | form | Liquid | | color | Clear light yellow | | Specific Gravity | 1.249 | | BRN | 118157 | | InChI | 1S/C6H10O2S2/c1-2-8-5(7)6-9-3-4-10-6/h6H,2-4H2,1H3 | | InChIKey | OMCSHTHLIQOHDD-UHFFFAOYSA-N | | SMILES | CCOC(=O)C1SCCS1 | | CAS DataBase Reference | 20461-99-8(CAS DataBase Reference) |
| Safety Statements | 23-24/25 | | RIDADR | 3334 | | WGK Germany | 3 | | F | 8-9 | | HS Code | 29349990 | | Storage Class | 10 - Combustible liquids |
| | ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE Usage And Synthesis |
| Chemical Properties | clear light yellow liquid | | Uses | Ethyl 1,3-dithiolane-2-carboxylate is an α-keto acid equivalent. It participates in the conjugate additions to enones. It is a bulky equivalent of acetate undergoing syn-selective aldol reactions. Anion derived from ethyl 1,3-dithiolane-2-carboxylate participates as nucleophile during the total synthesis of the corynanthe alkaloid dihydrocorynantheol and the formal syntheses of the indole alkaloids tacamonine, rhynchophylline and hirsutine. It also participates in the conjugate addition of enolates to phenylglycinol-derived α,β-unsaturated δ-lactams. | | General Description | Ethyl 1,3-dithiolane-2-carboxylate is an α-keto acid equivalent. It participates in the conjugate additions to enones. It is a bulky equivalent of acetate undergoing syn-selective aldol reactions. Anion derived from ethyl 1,3-dithiolane-2-carboxylate participates as nucleophile during the total synthesis of the corynanthe alkaloid dihydrocorynantheol and the formal syntheses of the indole alkaloids tacamonine, rhynchophylline and hirsutine. It also participates in the conjugate addition of enolates to phenylglycinol-derived α,β-unsaturated δ-lactams. | | Purification Methods | Dissolve the ester in CHCl3, wash it with aqueous K2CO3, twice with H2O, dry it over MgSO4, filter, evaporate and distil the residue in vacuo. [Hermann et al Tetrahedron Lett 2599 1973, Corey & Erickson J Org Chem 36 3553 1971]. [Beilstein 19/7 V 225.] |
| | ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE Preparation Products And Raw materials |
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