HCID 68826039, compound → HCID 57602832, compound

HRID 1788384Notes

Reaction equation

HRID 1788384 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1([CH3:12])[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.[H][H]>CO.[C].[Pd]>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1([CH3:12])[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 68826039HCID 68826039, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57602832HCID 57602832, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 220 g (1.19 mmol) of 3-(4-methyltetrahydropyran-4-yl)acrylic acid methyl ester in methanol (15 mL) was added 40 mg of palladium-carbon, replaced with hydrogen gas, and then stirred for 12 hours at room temperature. After the reaction mixture was filtered through Celite, the solvent was removed under a reduced pressure. The obtained residue was purified by column chromatography (silica gel 20 g, developing solvent: ethyl acetate) to obtain 222 mg (yield 100%) of 3-(4-methyltetrahydropyran-4-yl)propionic acid methyl ester (IX-144). Its physical property is shown below.

Workup

  1. filtrationAfter the reaction mixture was filtered through Celite
  2. customthe solvent was removed under a reduced pressure
  3. customThe obtained residue was purified by column chromatography (silica gel 20 g, developing solvent: ethyl acetate)

Sources & evidence

ORD record
ord-cdadb8e507934b2e8863900d7f05c0be
Source dataset
uspto-grants-2009_03
Patent number
US07511144B2

Reaction notes

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