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Tetrahydrofuran → 4,5-Dihydroxy-pentanoic Acid Ethyl Ester
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Tetrahydrofuran | HCID 8028 | — |
| 反応物 | Ethyl 4-pentenoate | HCID 74786 | — |
| 反応物 | Methyl morpholine oxide | HCID 82029 | — |
| 反応物 | Dichloromethane methanol | HCID 21226129 | — |
| 触媒 | Osmium Tetroxide | HCID 30318 | — |
| 溶媒 | Water | HCID 962 | — |
| 生成物 | 4,5-Dihydroxy-pentanoic Acid Ethyl Ester | HCID 57093956 | 96% |
反応手順
A solution of ethyl pent-4-enoate (11.7 g, 91.3 mmol) in tetrahydrofuran (420 mL) and water (40 mL) is treated with osmium tetroxide (1.0 g, 4.2 mmol) and 4-methylmorpholine N-oxide (32.5 mL, 50% in water) at room temperature and stired for 3 h, at which time no more starting material is detectable by TLC (SiO2, 2% methanol/dichloromethane, Rf=0.40). The mixture is concentrated in vacuo and the residue chromatographed on SiO2 (2% methanol/ethyl acetate) to afford the title compound 14.37 g (96%) as a colorless oil.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07087626B2 |
| 出典データセット | uspto-grants-2006_08 |
| ORD ID | ord-57fb327c6424452aa0687ad11e5803ae |
| 出典メモ | uspto-grants-2006_08 |