Water → HCID 86668663, compound

HRID 73642Notes

Reaction equation

HRID 73642 reaction equation
[CH:1]([C:3]1[CH2:4][CH2:5][CH2:6][O:7][CH:8]=1)=[CH2:2].[CH:9]([CH:11]=[CH2:12])=[O:10].O>C(Cl)Cl>[O:7]1[C@H:8]2[C:3](=[CH:1][CH2:2][CH2:12][C@H:11]2[CH:9]=[O:10])[CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 7847AcroleinHCID 111593065-ethenyl-3,4-dihydro-2H-pyran

Product 1

HCID 86668663HCID 86668663, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.613 g 5-ethenyl-3,4-dihydro-2H-pyran and 8.9 mL acrolein (90% pure) was dissolved in 39 mL CH2Cl2 and stirred overnight at RT. The reaction was added to water and extracted with CH2Cl2. The crude extract was filtered, concentrated using a rotovap, then purified on silica gel to provide the title compound. 1H NMR (500 MHz, CDCl3) δ=1.64-1.98 (m, 5H), 2.04-2.16 (m, 1H), 2.23-2.29 (m, 1H), 2.34-2.38 (m, 1H), 2.60-2.64 (m, 1H), 3.55-3.61 in, 1H), 3.99-4.04 (m, 1H), 4.21 (d, J=5.6 Hz, 1H), 5.55 (s, 1H), 9.88 (s, 1H) ppm.

Workup

  1. extractionextracted with CH2Cl2
  2. extractionThe crude extract
  3. filtrationwas filtered
  4. concentrationconcentrated
  5. custompurified on silica gel

Sources & evidence

ORD record
ord-ee249820998f4a37aeca2df7489170b5
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

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