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Volumn , Issue 3, 2007, Pages 491-493

Scandium triflate catalyzed transesterification of carboxylic esters

Author keywords

Carboxylic esters; Catalysis; Scandium; Transesterification

Indexed keywords

2 PROPANOL; ALCOHOL; ALLYL ALCOHOL; ESTER; METHANOL; SCANDIUM; SCANDIUM TRIFLATE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ESTERIFICATION; MICROWAVE IRRADIATION;

EID: 33847390296 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-967936 Document Type: Article

Times cited : (25)

References (14)

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- Excellent review: Otera, J. Esterification; Wiley-VCH: Weinheim, 2003.
- Excellent review: Otera, J. Esterification; Wiley-VCH: Weinheim, 2003.

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- Specialized reviews about transesterification: (a) Otera, J. Chem. Rev. 1993, 93, 1449.
- Specialized reviews about transesterification: (a) Otera, J. Chem. Rev. 1993, 93, 1449.

3
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- Seebach, D.¹ Hungerbühler, E.² Naef, R.³ Schnurrenberger, P.⁴ Weidmann, B.⁵ Züger, M.⁶

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- Otera, J.¹ Yano, T.² Kawabata, A.³ Nozaki, H.⁴

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- Orita, A.¹ Nagano, Y.² Hirano, J.³ Otera, J.⁴

11
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- At room temperature no full conversion could be achieved even with 10 mol% catalyst and prolonged reaction times
- At room temperature no full conversion could be achieved even with 10 mol% catalyst and prolonged reaction times.

12
- 33847399609
- Typical Experimental Procedure. A solution of the ester (1.00 mmol) in the respective alcohol (10 mL) was treated with 49.0 mg (0.10 mmol, 10 mol, Sc(OTf)3 and refluxed for the indicated reaction time. The reaction mixture was cooled to r.t. and filtered over a short plug of silica gel. All volatiles were evaporated in vacuo and the residue was purified by chromatography with mixtures of Et2O and pentane. All esters prepared were characterized by NMR, IR, and MS and gave spectroscopic data matching the reported data. The ee values of the (S)-mandelate esters were determined by HPLC on a chiral OD-phase with hexane-i-PrOH, 90:10, flow rate 1.0 mL/min. The ee of (R)-methyl β-hydroxy butyrate was determined by 19F NMR analysis of the corresponding Mosher ester. For the microwave experiments a microwave reactor 'microPREP A, MLS GmbH, Germany) with a single magnetron max. 1200 W, pulsed irradiation, 2.45 GHz, terminal 3
- 19F NMR analysis of the corresponding Mosher ester. For the microwave experiments a microwave reactor 'microPREP A' (MLS GmbH, Germany) with a single magnetron (max. 1200 W, pulsed irradiation, 2.45 GHz), terminal 320 controller, and easy CONTROL 06 software was used. An internal ATC-FO 300 fiberoptic sensor inserted into the reaction vessel was employed to measure the temperature inside the reaction mixture accurately and adjust the temperature to the set temperature automatically.

13
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- Excellent review about microwave-accelerated reactions: Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250;
- Excellent review about microwave-accelerated reactions: Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250;

14
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- Angew. Chem. 2004, 116, 6408.
- (2004) Chem , vol.116 , pp. 6408
- Angew¹

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