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Volumn , Issue 16, 2008, Pages 2425-2428

An efficient and solvent-free synthesis of mixed ortho esters

Author keywords

1,2 diols; Alcohols; Cyano hydrins; Ketene dimethyl acetal; Ortho esters

Indexed keywords

ACETAL DERIVATIVE; ALCOHOL DERIVATIVE; ESTER DERIVATIVE; SOLVENT;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; ELECTRON TRANSPORT; SYNTHESIS;

EID: 54149090820 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078215 Document Type: Article

Times cited : (4)

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31
- 54149091751
- Compound 16: yellow oil. 1H NMR (400 MHz, C 6D6, δ, 6.00 (ddd, 1 H, 3J trans, 17.4 Hz, 3Jcis, 10.6 Hz, 3J, 6.1 Hz, 5.32 (br dt, 1 H, 3J trans, 17.2 Hz, 2J, 1.5 Hz, 4J, 1.5 Hz, 5.06 (ddd, 1 H, 3J cis, 10.6 Hz, 2J, 1.8 Hz, 4J, 1.4 Hz, 4.57 (qt, 1 H, 3J, 6.1 Hz, 4J, 1.3 Hz, 3.79 (dd, 1 H, 2J, 9.7 Hz, 3J, 6.1 Hz, 3.62 (dd, 1 H, 2J, 9.7 Hz, 3J, 5.9 Hz, 3.20 (s, 3 H, 3.19 (s, 3 H, 3.17 (s, 3 H, 3.16 (s, 3 H, 1.42 (s, 3 H, 1.34 (s, 3 H, 13C NMR (100 MHz, C 6D6, δ, 138.7, 128.9, 115.4, 114.8, 72.6, 66.0, 49.8, 49.7, 49.6, 49.5, 20.8, 19.4. MS ESI, m/z, 287 [M
- 6: 287.1470; found: 287.1454.

32
- 54149117060
- In a typical experiment, ketene dimethyl acetal (3 mmol per hydroxyl group) was added cautiously to the anhyd alcohol (1 mmol) and stirred rapidly at r.t. under argon for 30 min. The reaction was followed by neutral alumina TLC. After complete conversion into the mixed ortho ester, the excess ketene dimethyl acetal was removed in vacuo resulting in pure mixed ortho ester in quantitative yield. Toluene-d8 and C6D6 were used for most NMR samples because trace amounts of HCl in CDCl3 resulted in decomposition of the mixed ortho ester.33
- 33

33
- 54149090179
- 13C NMR and/or HRMS and elemental analysis.
- 13C NMR and/or HRMS and elemental analysis.

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