関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Sodium Hydroxide | HCID 14798 | — |
| 反応物 | L-Proline | HCID 145742 | — |
| 反応物 | Sodium methanesulfinate | HCID 2733271 | — |
| 反応物 | (S)-(7-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol | HCID 23394142 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 溶媒 | Dimethyl Sulfoxide | HCID 679 | — |
| 生成物 | [(2S)-7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methanol | HCID 66879136 | 213.6% |
反応手順
A mixture of [(2S)-7-bromo-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (0.6 g, 2.3 mmol), sodium methanesulfinate (85%) (0.4 g, 3.4 mmol), CuI (0.043 g, 0.2 mmol), L-proline (0.052 g, 0.5 mmol) and NaOH (0.018 g, 0.5 mmol) in DMSO (3 ml) was heated under microwave radiation at 140° C. for 2 h 30 min in a nitrogen-flushed vial. The mixture was mixed with 2 other batches and water and EtOAc was added. The solution was extracted with EtOAc (3×50 ml). The combined organic phases were washed with LiCl (5%), HCl (1 N) and brine. The resulting solution was dried (Na2SO4) and evaporated to dryness. Purification on flash column chromatography (isooctane/EtOAc) gave the title compound (1.2 g). MS m/z (rel. intensity, 70 eV) 244 (M+, bp), 213 (39), 165 (26), 134 (22), 79 (23).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08524766B2 |
|---|
| 出典データセット | uspto-grants-2013_09 |
|---|
| ORD ID | ord-03f4373c7a4a4431bff4e8401daf1f70 |
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| 出典メモ | uspto-grants-2013_09 |
|---|
