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Sodium Hydroxide → t-Butyldimethylsilyloxy-2,6-dipropyl-4-(2-hydroxyethyl)-benzene
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Sodium Hydroxide | HCID 14798 | — |
| 反応物 | Sodium peroxide | HCID 14803 | — |
| 反応物 | Borane;tetrahydrofuran | HCID 2723981 | — |
| 反応物 | t-Butyldimethylsilyloxy-2,6-dipropyl-4-vinyl benzene | HCID 19080390 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | t-Butyldimethylsilyloxy-2,6-dipropyl-4-(2-hydroxyethyl)-benzene | HCID 19080442 | — |
反応手順
To a solution of 475 mg (1.48 mmol) of the product of Step B in 3 mL of THF at 0° C. was added 1.6 mL (1.62 mmol) of a 1N borane/THF solution. After 1 hour TLC indicated that the starting material had been consumed. The reaction mixture was quenched with 3 drops of methanol and then 0.70 mL (6.22 mmol) of 30% sodium peroxide and 6.2 mL (6.2 mmol) of 1N sodium hydroxide were added. After two hours the reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was then dried over sodium sulfate, filtered and concentrated. Flash chromatography (silica gel, hexane/ethyl acetate 4:1) gave 265 mg of the title compound as a clear oil.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05767310 |
| 出典データセット | uspto-grants-1998_06 |
| ORD ID | ord-3be3864fbe1a499ba250d3597a74a1fd |
| 出典メモ | uspto-grants-1998_06 |