HCID 57835929, compound → HCID 57835819, compound

HRID 922300Notes

Reaction equation

HRID 922300 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9]\[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1>C(O)C.C(OCC)(=O)C.[Pd]>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 57835929HCID 57835929, compound

Product 1

HCID 57835819HCID 57835819, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A 500 mL par shaker charged with ethyl (2Z)-3-(4-hydroxyphenyl)-3-phenylprop-2-enoate (1 g, 3.7 mmol) in Ethanol/Ethyl acetate was degasified with nitrogen for 2 min. Added 10% of Pd/C (0.4 g, 10%) and applied 50 psi of H2 pressure for 3 h. Reaction mixture was filtered through celite pad and washed the pad with excess Ethanol. Organic phase was dried over anhydrous Na2SO4 and concentrated to afford oil as product. (0.6 g, Yield: 60.1%); 1H NMR (300 MHz, DMSO-d6): δ 9.21 (s, 1H), 7.07-7.29 (m, 7H), 6.63-6.66 (d, 2H), 4.29-4.34 (t, 1H), 3.89-3.96 (q, 2H), 3.02-3.03 (d, 2H), 0.99-1.04 (t, 3H)

Workup

  1. customfor 3 h
  2. customReaction mixture
  3. filtrationwas filtered through celite pad
  4. washwashed the pad with excess Ethanol
  5. dry with materialOrganic phase was dried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customto afford oil as product

Sources & evidence

ORD record
ord-1676c50a58494074b133a6455d0deb2a
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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