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Potassium Carbonate → [(2R)-7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methanol
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | L-Proline | HCID 145742 | — |
| 反応物 | Sodium methanesulfinate | HCID 2733271 | — |
| 反応物 | (R)-(7-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol | HCID 66879096 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 溶媒 | Dimethyl Sulfoxide | HCID 679 | — |
| 生成物 | [(2R)-7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methanol | HCID 66878426 | 78.2% |
反応手順
Two batches of [(2R)-7-bromo-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (2.2 g, 8.9 mmol), sodium methanesulfinate (85%) (1.6 g, 13.3 mmol), CuI (0.2 g, 0.9 mmol), L-proline (0.2 g, 1.8 mmol) and K2CO3 (0.2 g, 1.8 mmol) in DMSO (20 ml) were heated under microwave radiation at 140° C. for 3 h in nitrogen-flushed vials. Water and EtOAc were added. The water layer was extracted with EtOAc (3×100 ml) and the combined organic phases were washed with LiCl (5%), HCl (1 N) and brine. The resulting solution was dried (Na2SO4) and evaporated to dryness. The residue was purified by flash column chromatography (isooctane/EtOAc) to give the title compound (1.7 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-4c5db21f63e6492c829c6c16c4269287 |
| 出典メモ | uspto-grants-2013_09 |