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Volumn 36, Issue 8, 2007, Pages 992-993

Benzyl N-phenyl-2,2,2-trifluoroacetimidate: A new and stable reagent for O-benzylation

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EID: 34548311880 PISSN: 03667022 EISSN: None Source Type: Journal
DOI: 10.1246/cl.2007.992 Document Type: Article

Times cited : (19)

References (18)

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17
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- The procedure for the preparation of 3 is as follows: To the stirred suspension of BnOH (2.34 g, 21.7 mmol) and 4 (5.00g, 24.1 mmol) in CH2Cl2 (120mL, NaH (964mg, 24.1 mmol) was added at 0°C. The mixture was stirred for 2 h at rt. After an addition of H 2O (0.1 mL, the mixture was evaporated and diluted with hexane (50 mL, The resulting mixture was filtered through a cotton-Celite pad, and the filtrate was evaporated. The resulting residue was purified by neutral silica-gel column chromatography (100 g of SiO2: Silica Gel 60N, pH 6.5-7.5, 40-50 μm, Kanto Chemical Co, Inc, hexane/Et20 50/1) to afford 3 (5.93 g, 98, as pale yellow oil at rt, mp 19-20°C; 1H NMR (400 MHz in CDCl3, δ 7.48-7.38 (m, 5H, 7.33 (dddd, J, 7.3, 6.7, 2.3, 2.3 Hz, 2H, 7.13 (ddd, J, 7.6, 7.3, 1.2 Hz, 2H, 6.85 (br d, J, 8.0 Hz, 2H, 5.34 (s, 2H, 13C NMR 100 MHz in CDCl3
- C-F = 285.1 Hz), 69.8.

18
- 34548370046
- The trichloroacetimidate 1 can be stored at 5 °C as solutions in hexane for periods of up to 2 months: see Ref. 4b.
- The trichloroacetimidate 1 can be stored at 5 °C as solutions in hexane for periods of up to 2 months: see Ref. 4b.

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