関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Water | HCID 962 | — |
| 反応物 | 4-Toluenesulfonyl chloride | HCID 7397 | — |
| 反応物 | trans-2-Butene-1,4-diol | HCID 175854 | — |
| 反応物 | Sodium t-butoxide | HCID 23676156 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | (e)-1,4-Ditosyloxy-2-butene | HCID 18320921 | 182% |
反応手順
To a solution of (E)-2-buten-1,4-diol (326 mg, 3.7 mmol) and p-toluenesulfonyl chloride (1.76 g, 9.25 mmol) in 30 mL of THF was added portionwise sodium tert-butoxide (1.07 g, 11.1 mmol)) under stirring at 0° C. The mixture was then stirred overnight at rt. Water (100 mL) was added and the product was extracted with CH2CL2 (3×25 mL). The extract was dried with MgSO4, filtered, and evaporated. Purification by flash column chromatography with hexane:ether:CH2CH2/3:1:1 gave the product as a crystal (1.21 g, 182%), m.p. 90-91° C. 1H NMR (300 MHz, CDCl3) δ 7.77 (d, J=8.7 Hz, 4H), 7.35 (d, J−8.4 Hz, 4H), 5.75-5.73 (m, 2H), 4.49-4.47 (m, 4H), 2.46 (s, 6H; Anal. Calcd for C18H20O6S2: C, 54.53; H, 5,08,found C, 54.61; H, 5.07.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US06344179B1 |
|---|
| 出典データセット | uspto-grants-2002_02 |
|---|
| ORD ID | ord-c47b6ed2961c4c2db566355e29457ec2 |
|---|
| 出典メモ | uspto-grants-2002_02 |
|---|
