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Malonic Acid → (2E)-3-[(2S)-2-methyltetrahydro-2H-pyran-4-yl]acrylic acid

HRID 1434605
Notes
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Reaction equation

HRID 1434605 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]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 57936012(2S)-2-methyltetrahydro-2H-pyran-4-carboxaldehyde

Product 1

HCID 57935998(2E)-3-[(2S)-2-methyltetrahydro-2H-pyran-4-yl]acrylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethyl acetate (100 ml) and 1N HCl
  3. customThe organic layer was dried
  4. customevaporated
  5. customrecrystallised
  6. customform toluene

Sources & evidence

ORD record
ord-63a828e8647f4fb991274297a980ec5f
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07615555B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes