Malonic Acid → (2E)-3-[(2S)-2-methyltetrahydro-2H-pyran-4-yl]acrylic acid
반응식
[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]1참가 물질
5
반응 조건
- 온도
- 100 °C
실험 절차
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).
후처리
- concentrationThe reaction mixture was concentrated
- custompartitioned between ethyl acetate (100 ml) and 1N HCl
- customThe organic layer was dried
- customevaporated
- customrecrystallised
- customform toluene
출처 및 근거
- ORD 기록
- ord-63a828e8647f4fb991274297a980ec5f
- 출처 데이터셋
- uspto-grants-2009_11
- 특허 번호
- US07615555B2
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