Benzyl 2-(2-pyridyloxy)-2-methylbutanoate → HCID 22270592, compound

HRID 1160698Notes

Reaction equation

HRID 1160698 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]([CH3:21])([CH2:19][CH3:20])[C:9]([O:11]CC1C=CC=CC=1)=[O:10]>[Pd].CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]([CH3:21])([CH2:19][CH3:20])[C:9]([OH:11])=[O:10]

Participants

4

Reactant 1

HCID 22270398Benzyl 2-(2-pyridyloxy)-2-methylbutanoate

Product 1

HCID 22270592HCID 22270592, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 2-(2-pyridyloxy)-2-methylbutanoate (1.6 g, 5.5 mmol) and 10% palladium on carbon (50 mg) in 50 mL MeOH was degassed and filled with hydrogen using a balloon. After stirring at room temperature overnight, the reaction mixture was filtered through CELITE diatomaceous earth and washed with MeOH (20 mL), and the filtrate was concentrated to dryness to give the title compound. 1H NMR (500 MHz, CD3OD): δ 8.03 (dd, 1H), 7.64 (ddd, 1H), 6.89 (dd, 1H), 6.76 (dd, 1H), 2.14 (m, 1H), 1.94 (m, 1H), 1.64 (s, 3H), 0.99 (t, 3H). LC-MS: m/e 196 (M+H)+ (1.8 min).

Workup

  1. customwas degassed
  2. additionfilled with hydrogen using a balloon
  3. filtrationthe reaction mixture was filtered through CELITE diatomaceous earth
  4. washwashed with MeOH (20 mL)
  5. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-8bca765b02df42fe90a9d23ae510e02c
Source dataset
uspto-grants-2010_10
Patent number
US07816534B2

Reaction notes

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