Malonic Acid → (2E)-3-[(2S)-2-methyltetrahydro-2H-pyran-4-yl]acrylic acid
反応式
[CH3:1][C@H:2]1[CH2:7][CH:6]([CH:8]=O)[CH2:5][CH2:4][O:3]1.C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13].N1CCCCC1>N1C=CC=CC=1>[CH3:1][C@H:2]1[CH2:7][CH:6](/[CH:8]=[CH:11]/[C:12]([OH:14])=[O:13])[CH2:5][CH2:4][O:3]1参加物
5
反応条件
- 温度
- 100 °C
実験手順
A mixture of (2S)-2-methyltetrahydro-2H-pyran-4-carboxaldehyde (4.0), malonic acid (6.495 g) and piperidine (0.1 ml) in pyridine (10 ml) was heated to 100° C. for 4 hours. The reaction mixture was concentrated and partitioned between ethyl acetate (100 ml) and 1N HCl. The organic layer was dried, evaporated and recrystallised form toluene to give the title compound. Yield 2.48 g. NMR CDCl3 1.2 (m, 4H), 1.5 (m, 1H), 1.7 (m, 2H), 2.45 (m, 1H), 3.5 (m, 2H), 4.05 (m, 1H), 5.8 (d, 1H), 7.0 (dd, 1H).
後処理
- concentrationThe reaction mixture was concentrated
- custompartitioned between ethyl acetate (100 ml) and 1N HCl
- customThe organic layer was dried
- customevaporated
- customrecrystallised
- customform toluene
出典と根拠
- ORDレコード
- ord-63a828e8647f4fb991274297a980ec5f
- 出典データセット
- uspto-grants-2009_11
- 特許番号
- US07615555B2
反応ノート
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