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Dimethyl Sulfoxide → (2-Ethoxycarbonyl)-(1-formyl)ethylene oxide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Dimethyl Sulfoxide | HCID 679 | — |
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | Oxalyl chloride | HCID 65578 | — |
| 反応物 | Ethyl acetate pentane | HCID 22335286 | — |
| 反応物 | (2-Ethoxycarbonyl)-(1-hydroxymethyl) ethylene oxide | HCID 88418003 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 溶媒 | Sodium chloride; water | HCID 57417360 | — |
| 生成物 | (2-Ethoxycarbonyl)-(1-formyl)ethylene oxide | HCID 88418014 | 80% |
反応手順
The procedure described by Evans and Williams European Patent Application No. 89302778.9, Publication No. 0334593 was employed for the Swern oxidation of (2-ethoxycarbonyl)-(1-hydroxymethyl) ethylene oxide (5.00 g) in methylene chloride (total 170 ml) with dimethylsulfoxide (7.3 mL), oxalyl chloride (4.2 mL) and triethylamine. Extractive work-up involving brine (150 mL), followed by trituration of impurities with pentane-ethyl acetate (2: 1, 450 mL ) afforded the title aldehyde (4.0 g, 80%). This material is used immediately and/or stored in dry methylene chloride at -25° C. under nitrogen.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05453504 |
| 出典データセット | uspto-grants-1995_09 |
| ORD ID | ord-34488c306dfd4c90ab0c205085cee601 |
| 出典メモ | uspto-grants-1995_09 |