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85037956782
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Typical experiment: a mixture of 4H-pyran 1 (200 mg, 0.88 mmol) and ethyl pyruvate (1.77 mmol, 2.0 equiv.) in benzene (30 ml) was irradiated at 350 nm (Rayonet, T=30°C) during 5 h. After evaporation in vacuo, the residue was purified by flash chromatography (petroleum ether:ethyl acetate 90:10) to give the α-hydroxy ester 2c (185 mg, 62%)
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Typical experiment: a mixture of 4H-pyran 1 (200 mg, 0.88 mmol) and ethyl pyruvate (1.77 mmol, 2.0 equiv.) in benzene (30 ml) was irradiated at 350 nm (Rayonet, T=30°C) during 5 h. After evaporation in vacuo, the residue was purified by flash chromatography (petroleum ether:ethyl acetate 90:10) to give the α-hydroxy ester 2c (185 mg, 62%).
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10
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85037953098
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13C NMR)
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13C NMR).
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11
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85037961668
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note
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-1): 3494, 1732, 1651, 1603.
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12
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85037952986
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-1): 1727, 1611. This oxidation by-product 3 was also observed when a solution of 4H-pyran 1 in AcOEt was stored at room temperature, under air atmosphere, during several days.
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-1): 1727, 1611. This oxidation by-product 3 was also observed when a solution of 4H-pyran 1 in AcOEt was stored at room temperature, under air atmosphere, during several days.
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13
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85037954138
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nJ) at 500 MHz spectrometer
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nJ) at 500 MHz spectrometer.
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15
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84984224538
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(b)
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17
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0343893183
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(d) Ryang, H.-S.; Shima, K.; Sakurai, H. J. Am. Chem. Soc. 1971, 93, 5270-5271.
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18
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0042011731
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(e)
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(e) Turro, N. J.; Shima, K.; Chung, C.-J.; Tanielian, C.; Kanfer, S. Tetrahedron Lett. 1980, 21, 2775-2778.
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Turro, N.J.1
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19
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33749100588
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(f)
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(f) Abe, M.; Shirodai, Y.; Nojima, M. J. Chem. Soc., Perkin Trans. 1 1998, 3253-3260.
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Abe, M.1
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20
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33646507198
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(a) Buschmann, H.; Scharf, H.-D.; Hoffmann, N.; Plath, M. W.; Runsink, J. J. Am. Chem. Soc. 1989, 111, 5367-5373.
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22
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(c)
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(c) Bach, T. Synthesis 1998, 683-703.
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(d) Griesbeck, A. G.; Mauder, H.; Stadtmüller, S. Acc. Chem. Res. 1994, 27, 70-75.
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Griesbeck, A.G.1
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