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3,4-dihydro-2H-pyran → 2-(5-Bromo-2-methyl-2-phenylpentyloxy)-tetrahydropyran
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 3,4-dihydro-2H-pyran | HCID 8080 | — |
| 反応物 | 2-(6-Bromo-2-methyl-2-phenylhexyloxy)-tetrahydropyran | HCID 11210453 | — |
| 反応物 | 5-Bromo-2-methyl-2-phenylpentan-1-ol | HCID 11345892 | — |
| 触媒 | p-Toluenesulfonic acid monohydrate | HCID 521998 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | 2-(5-Bromo-2-methyl-2-phenylpentyloxy)-tetrahydropyran | HCID 11484608 | 95% |
反応手順
According to the method described for the synthesis of 207d, 206b (20.0 g, 77.8 mmol) was treated with 3,4-dihydro-2H-pyran (8.2 g, 96.5 mmol) and p-toluenesulfonic acid hydrate (0.57 g, 3.0 mmol) in CH2Cl2 (350 mL) to afford 207b (25.2 g, 95%) as an oil, which was used without further purification. 1H NMR (CDCl3): 7.26-7.08 (m, 5 H), 4.45 (m, 1 H), 3.72 (m, 1 H), 3.58 (m, 1 H), 3.35-3.05 (m, 2 H), 3.28 (t, 2 H, J=6.6), 1.95-1.39 (m, 10 H), 1.25 (s, 3 H). 13C NMR (CDCl3): δ 145.38, 128.15, 126.51, 126.03, 99.06, 98.92, 76.20, 61.91, 61.80, 41.82, 41.74, 37.58, 37.43, 34.65, 30.61, 27.88, 25.58, 23.03, 22.90, 19.39, 19.32. HRMS (LSIMS, nba): Calcd for C17H26O2Br (MH+): 341.1116, found: 341.1127.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08642653B2 |
| 出典データセット | uspto-grants-2014_02 |
| ORD ID | ord-67f114da9bb64f9c9e02cedf7ed3abad |
| 出典メモ | uspto-grants-2014_02 |