関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Diglyme | HCID 8150 | — |
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | (1S,2R,4aS,8aS)-1-(hydroxymethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol | HCID 10879261 | — |
| 反応物 | 1-Iodo-3,5-bis(propan-2-yloxy)benzene | HCID 58294816 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | (1S,2R,4aS,8aS)-1-[3,5-bis(propan-2-yloxy)phenoxymethyl]-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol | HCID 58294796 | 66% |
反応手順
In a sealed tube purged with nitrogen, compound (47) (1.85 g, 5.78 mmol), (1S,2R,4aS,8aS)-1-(hydroxymethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (3) (1.26 g, 5.25 mmol), Cs2CO3 (2.56 g, 7.87 mmol), 3,4,7,8-tetramethyl-[1,10]-phenylthroline (0.25 g, 1.0 mmol), CuI (0.10 g, 0.70 mmol), diglyme (5 mL) and toluene (20 mL) were placed. The reaction mixture was stirred at 120° C. for 18 h. The reaction was cooled to room temperature, diluted with EtOAc (600 mL) and washed with water (200 mL). The solid material was removed by filtration. The organic layer was separated, dried (Na2SO4) and concentrated. Purification by column chromatography on silica gel (Hexanes/EtOAc, 4:1) gave (1S,2R,4aS,8aS)-1-[3,5-bis(propan-2-yloxy)phenoxymethyl]-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (48) (1.50 g, 66%) as a colourless oil.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08101605B2 |
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| 出典データセット | uspto-grants-2012_01 |
|---|
| ORD ID | ord-08f1a9d1c0844460a5e8342c80ff4fc6 |
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| 出典メモ | uspto-grants-2012_01 |
|---|
