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Volumn 36, Issue 4, 2007, Pages 532-533

One-pot synthesis of α-alkoxy azides from carbonyl compounds catalyzed by iron(III) chloride

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EID: 34248520637 PISSN: 03667022 EISSN: None Source Type: Journal
DOI: 10.1246/cl.2007.532 Document Type: Article

Times cited : (8)

References (14)

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13
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- Typical experimental procedure for the synthesis of α-benzyloxy azides from aliphatic aldehydes as follows: To a suspension of anhydrous iron(III) chloride (3.7 mg, 0.023 mmol) and 3-phenylpropionaldehyde (61.9 mg, 0.46 mmol) in acetonitrile (2 mL) were added benzyloxytrimethylsilane (108 μL, 0.55 mmol) and trimethylsilyl azide (83.3 mg, 0.72 mmol) in acetonitrile (1 mL) under argon atmosphere. After stirring for 1 h at -40°C, the reaction mixture was quenched with a phosphate buffer (pH 7, The organic materials were extracted with CH2Cl2, washed with brine, and dried over Na2SO4. 1-Benzyloxy-3-phenylpropyl azide 112.6 mg, 91, was isolated by thin-layer chromatography on silica gel
- 4. 1-Benzyloxy-3-phenylpropyl azide (112.6 mg, 91%) was isolated by thin-layer chromatography on silica gel.

14
- 34248534239
- Typical experimental procedure for the synthesis of α-benzyloxy azides from aromatic aldehydes as follows: To a suspension of anhydrous iron(III) chloride (1.5 mg, 0.0093 mmol) and benzaldehyde (47 μL, 0.46 mmol) was added benzyloxytrimethylsilane (220 μL, 1.1 mmol) and stirred at 0°C under argon atmosphere. After 2 h, trimethylsilyl azide (95 μL, 0.72 mmol) in propionitrile (1.5 mL) was added and stirred for 1 h at -78°C. The reaction mixture was quenched with a phosphate buffer (pH 7, The organic materials were extracted with CH2Cl2, washed with brine, and dried over Na2SO4, α-Azido-α-benzyloxymethyl)benzene 103.5 mg, 94, was isolated by thin-layer chromatography on silica gel
- 4. (α-Azido-α-benzyloxymethyl)benzene (103.5 mg, 94%) was isolated by thin-layer chromatography on silica gel.

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