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Vinylcyclopentane → (3R,4R,5S)-5-[(1R,2E)-3-cyclopentyl-1-hydroxyprop-2-en-1-yl]-3-ethoxy-4-hydroxydihydrofuran-2(3H)-one
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Vinylcyclopentane | HCID 77345 | — |
| 反応物 | (3R,4R,5S)-3-ethoxy-4-hydroxy-5-[(1R)-1-hydroxyprop-2-en-1-yl]dihydrofuran-2(3H)-one | HCID 57617787 | — |
| 触媒 | HCID 178479819 | HCID 178479819 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | (3R,4R,5S)-5-[(1R,2E)-3-cyclopentyl-1-hydroxyprop-2-en-1-yl]-3-ethoxy-4-hydroxydihydrofuran-2(3H)-one | HCID 67329167 | 12.7% |
反応手順
550 mg of 51 (2.47 mmol), 0.987 g of vinylcyclopentane (10.26 mmol), 18 mL of CH2Cl2 and 63 mg of 2nd generation Grubb's catalyst (C46H65Cl2N2PRu, MW 848.98, 0.030 mmol) are added to a 50 mL round-bottomed flask. The medium is stirred for 24 h at RT and then the insoluble material is filtered and the solvent is evaporated. The crude product is chromatographed on a silica cartridge (40 g, eluent AcOEt/heptane—in an AcOEt gradient: 50 to 100%). 85 mg of expected product 52 are obtained.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07994161B2 |
| 出典データセット | uspto-grants-2011_08 |
| ORD ID | ord-c919a1a57ab24fdf8a2c35a477930053 |
| 出典メモ | uspto-grants-2011_08 |