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

HRID 2104268Notes

Reaction equation

HRID 2104268 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 of methanol 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 methanol (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 methanol (20 mL)
  5. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-d8719394feb547e487b71cd5061cdc8f
Source dataset
uspto-grants-2009_08
Patent number
US07576239B2

Reaction notes

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