Hydrochloric Acid → 1-Butoxymethyl-4-(2-nitroethyl)-benzene

To a solution of 4-butoxymethyl-benzaldehyde (7.39 g, 3.84 mmol) described in Manufacturing Example 4-1-2 in methanol (140 mL) was added nitromethane (2.70 mL, 49.9 mmol) followed by sodium methoxide (1.49 M methanol solution, 9.41 mL, 46.1 mmol) at 0° C. The reaction solution was stirred for 30 minutes at room temperature, and 5 N aqueous hydrochloric acid solution (120 mL) was added thereto and stirred for further 25 minutes. This reaction solution was partitioned into saturated aqueous sodium chloride and ethyl acetate at 0° C. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. To a solution of the resulting residue in dimethyl sulfoxide (100 mL) and acetic acid (6 mL) was added sodium borohydride (1.84 g, 46.1 mmol) at room temperature while cooling appropriately. This solution was then stirred for 80 minutes at room temperature. The reaction solution was partitioned into water and ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1) to obtain the title compound (2.68 g, 29%).

1. stirringstirred for further 25 minutes
2. customThis reaction solution was partitioned into saturated aqueous sodium chloride and ethyl acetate at 0° C
3. washThe organic layer was washed with saturated aqueous sodium chloride
4. dry with materialdried over anhydrous magnesium sulfate
5. customthe solvent was evaporated under a reduced pressure
6. temperaturewhile cooling appropriately
7. stirringThis solution was then stirred for 80 minutes at room temperature
8. customThe reaction solution was partitioned into water and ethyl acetate
9. washThe organic layer was washed with saturated aqueous sodium chloride
10. dry with materialdried over anhydrous magnesium sulfate
11. customthe solvent was evaporated under a reduced pressure
12. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1)

ORDレコード

ord-77e046fe2c7a4cb8afe5480ea95156af

出典データセット

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08153662B2