Malonic Acid → (2E)-3-[(2S)-2-methyltetrahydro-2H-pyran-4-yl]acrylic acid
Reaction equation
[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]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
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).
Workup
- concentrationThe reaction mixture was concentrated
- custompartitioned between ethyl acetate (100 ml) and 1N HCl
- customThe organic layer was dried
- customevaporated
- customrecrystallised
- customform toluene
Sources & evidence
- ORD record
- ord-63a828e8647f4fb991274297a980ec5f
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07615555B2
Reaction notes
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