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* Storage: Keep in dark place,Sealed in dry,Room Temperature
CAS No. : | 66-77-3 | MDL No. : | MFCD00004003 |
Formula : | C11H8O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SQAINHDHICKHLX-UHFFFAOYSA-N |
M.W : | 156.18 | Pubchem ID : | 6195 |
Synonyms : |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Stage #1: With sodium acetate; sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran for 12 h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water | To 1-naphthaldehyde (1.50 g, 9.62 mmol, 1.00 equiv) in 40 mL THF is added NaOAc (0.79 g, 9.62 mmol, 1.00 equiv), Me2NH-HCl (863 mg, 10.6 mmol, 1.10 equiv), and AcOH (0.11 mL, 1.9 mmol, 0.20 equiv) at 23 0C. NaBH(OAc)3 (4.08 g, 19.3 mmol, 2.00 equiv) is added in three portions over five minutes. The suspension is stirred for 12 hours before solvent is removed in vacuo. To the residue is added 10 mL sat. NaHCO3(aq) and 10 mL CH2Cl2. The phases are separated and the aqueous phase is extracted with CH2Cl2 (3 x 10 mL). The combined organic phase is concentrated in vacuo. The residue is purified by chromatography on silica gel eluting with hexanes/EtOAc 3:2 (v/v) to afford 1.64 g of the title compound as a colorless liquid (92percent yield). R/= 0.38 (hexane/EtOAc 2:3 (v/v)). NMR Spectroscopy: 1H NMR (600 MHz, CDCl3,23 0C, δ): 8.27 (d, J = 8.5 Hz, IH), 7.85 (d, J= 8.2 Hz, IH), 7.79 (dd, J= 6.7 Hz, 2.9 Hz, IH), 7.53 (ddd, J = 8.0 Hz, 6.5 Hz, 1.0 Hz, IH), 7.48 (ddd, J= 6.5 Hz, 5.5 Hz, 1.0 Hz, IH), 7.43- 7.40 (m, 2H), 3.82 (s, 2H), 2.31 (s, 6H). 13C NMR (125 MHz, CDCl3, 23 0C, δ): 134.85, 133.84, 132.52, 128.40, 127.95, 127.38, 125.98, 125.56, 125.06, 124.49, 62.60, 45.69. Mass <n="81"/>Spectrometry: HRMS-FIA (m/z): calcd for [Ci3Hi5N + H], 186.1277. Found, 186.1286. These spectroscopic data correspond to reported data (Gay, R.L.; Hauser, CR. J. Am. Chem. Soc. 1967, 89, 2297-2303; incorporated herein by reference). |
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