反応式
[CH2:1]([O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1)[C:2]#[CH:3].C([Mg]Br)C.[O:15]1[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]1>C1COCC1>[OH:21][C:18]1([C:3]#[C:2][CH2:1][O:4][CH:5]2[CH2:10][CH2:9][CH2:8][CH2:7][O:6]2)[CH2:19][CH2:20][O:15][CH2:16][CH2:17]1参加物
反応条件
- 温度
- -20 °C
実験手順
Tetrahydro-2-(2-propynyloxy)-2H-pyran (21 g, 150 mmol) was converted to the corresponding magnesium anion by deprotonation with ethyl magnesium bromide (75 mL of a 2M solution, 150 mmol) according to the method described in Org. Synth., 60: 81, 7 (1981). The resulting anion was cooled to -20° C. and tetrahydro-4H-pyran-4-one (14.8 g, 148 mmol) in dry THF (30 mL) was added dropwise and the resulting solution stirred for three hours. The reaction was quenched by addition of crushed ice and saturated aqueous NH4Cl. The resulting two-layered mixture was extracted with ether (3×150 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Purification by chromatography on silica gel (200 g, 20% ethyl acetate: hexanes) provided 4-hydroxy-4-[3-(tetrahydropyran-2-yloxy)prop-1-ynyl]tetrahydropyran(31.4 g, 88%).
後処理
- customThe reaction was quenched by addition of crushed ice and saturated aqueous NH4Cl
- extractionThe resulting two-layered mixture was extracted with ether (3×150 mL)
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customPurification by chromatography on silica gel (200 g, 20% ethyl acetate: hexanes)
出典と根拠
- ORDレコード
- ord-fc58a5611d344ef8933ea94ade1a5a7d
- 出典データセット
- uspto-grants-1995_06
- 特許番号
- US05426111
関連ノート
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