Methanol → HCID 14794005, compound

HRID 329484Notes

Reaction equation

HRID 329484 reaction equation
[OH:1][C:2]1C(=O)O[CH:5]=[CH:6][CH:7]=1.[CH3:9][O:10][C:11]([CH3:22])([CH3:21])[CH2:12][CH2:13][CH:14]=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].CO.[H][H]>C1(C)C=CC=CC=1.[Pd]>[C:16]([CH:15]1[CH:14]([CH2:13][CH2:12][C:11]([O:10][CH3:9])([CH3:21])[CH3:22])[CH2:5][CH2:6][CH2:7][C:2]1=[O:1])([O:18][CH2:19][CH3:20])=[O:17]

Participants

7

Reactant 4

HCID 887MethanolHCID 681302H-Pyran-4-one, 3-hydroxy-HCID 53765586HCID 53765586, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14794005HCID 14794005, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 3-Hydroxypyrone (obtained by the procedure of R. H. Wiley and C. H. Jorboe, J. Am. Chem. Soc., 78, 2398, (1956), 5.0 g, 0.045 mol) and ethyl 6-methoxy-6-methyl-2-heptenoate (8.9 g, 0.045 mol) were dissolved in toluene (15 mL) and heated in a sealed vessel for 7 hours at 200° C. After cooling 5% Pd/C (1.0 g) and methanol (50 mL) were added and the vessel was pressurized with hydrogen gas (200 psi). After stirring 20 hours the mixture was filtered and concentrated to the residue. The crude product decomposed on distillation. No further purification was attempted. NMR of crude material (CDCl3)δ1.2(s,6H), 1.3(t,3H), 3.2(s,3H), 3.7(m,1H), 4.2(m,2H); IR(neat) 2600-3800, (broad band), 2990, 2950, 1740, 1720, 1680, 1650, 1620, 1470, 1390, 1370, 1220, 1090 cm-1.

Workup

  1. customobtained by the procedure of R
  2. additionwere added
  3. filtrationwas filtered
  4. concentrationconcentrated to the residue
  5. distillationThe crude product decomposed on distillation
  6. customNo further purification

Sources & evidence

ORD record
ord-5cd4b5cf2d30473e8d74c55a91e2c7de
Source dataset
uspto-grants-1990_01
Patent number
US04891447

Reaction notes

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