HCID 10198689, compound → HCID 15638317, compound

HRID 1814360Notes

Reaction equation

HRID 1814360 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH:8]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)[O:7]1)=[O:5])[CH3:2].[H][H]>[OH-].[OH-].[Pd+2].C(O)C>[CH2:1]([O:3][C:4](=[O:5])[CH:6]([OH:7])[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)[CH3:2]

Participants

5

Reactant 2

HCID 10198689HCID 10198689, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15638317HCID 15638317, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To an ethanol (400 mL) solution of 3-naphthalen-1-yl-oxirane-2-carboxylic acid ethyl ester (21.26 g, 87.8 mmol) was added 5% palladium hydroxide on carbon (1.0 g). The reaction was then pressurized to 50 psi with hydrogen for 2 h. The reaction was then filtered through a celite pad. The cake was washed with ethanol (100 mL). The reaction was then concentrated under reduced pressure to yield 2-hydroxy-3-naphthalen-1-yl-propionic acid ethyl ester as an oil. 1H NMR(300 MHz, DMSO) 8.05 (d, 1H), 7.89(d, 1H), 7.79(d, 1H), 7.34 (m, 4H), 5.58 (d, 1H), 4.32 (dd, 1H), 4.04 (q, 2H), 3.44 (dd, 1H), 3.24 (dd, 1H), 1.05 (t, 3H).

Workup

  1. filtrationThe reaction was then filtered through a celite pad
  2. washThe cake was washed with ethanol (100 mL)
  3. concentrationThe reaction was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-58af7e7e2d7f4ba697beb4c118bba7f7
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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