ChemicalBook CAS DataBase List 2-AMINO-1-PHENYLETHANOL

2-AMINO-1-PHENYLETHANOL synthesis

9synthesis methods

Product Name:2-AMINO-1-PHENYLETHANOL
CAS Number:7568-93-6
Molecular formula:C8H11NO
Molecular Weight:137.18

96-09-3 Synthesis

96-09-3
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7568-93-6
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$13.43/500mgs:

Yield:7568-93-6 81%

Reaction Conditions:

Stage #1:styrene oxide with sodium hexamethyldisilazane in tetrahydrofuran at 0 - 25; for 20 h;
Stage #2: with water in tetrahydrofuran at 25; for 5 h;regioselective reaction;

Steps:

Representative procedure
General procedure: To a stirred solution of 2-phenyloxirane 5 (1 g, 8.31 mmol) in anhydrous tetrahydrofuran was added sodium bis(trimethylsilyl)amide (1 M solution in THF, 29.08 mL, 29.08 mmol, 3.0 equiv) at 0-5 °C. The resultant mixture was allowed to warm to 25 °C and stirred for 20 h, by which time the reaction was completed as indicated by TLC. The reaction mixture was then quenched with water (2.5 mL) and stirred for 5 h. The solvent was removed by distillation under reduced pressure bringing the total volume to one-fourth. The content of the reaction mixture was extracted with dichloromethane (2 × 10 mL). The organic layer was dried over anhydrous Na₂SO₄ and concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography on silica gel to obtain the pure product as pale yellow solid.

References:

Murugan, Andiappan;Kadambar, Vasantha Krishna;Bachu, Sreekanth;Rajashekher Reddy;Torlikonda, Venkatarao;Manjunatha, Sulur G.;Ramasubramanian, Sridharan;Nambiar, Sudhir;Howell, Gareth P.;Withnall, Jane [Tetrahedron Letters,2012,vol. 53,# 43,p. 5739 - 5741] Location in patent:supporting information

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