HCID 59464241, compound → HCID 178471538, compound

HRID 1713868Notes

Reaction equation

HRID 1713868 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][C:11](=[C:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>[Pd].CCOC(C)=O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:9][CH2:10][C@H:11]([CH:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 59464241HCID 59464241, compound

Product 1

HCID 178471538HCID 178471538, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% Palladium on carbon (250 mg) was added in one portion to a stirred solution of ethyl 2-[4-(4-hydroxyphenyl)cyclohexylidene]propanoate (6.9 g, 25.3 mmol) in EtOAc (50 mL) and the reaction mixture was stirred under a hydrogen atmosphere for 24 h. The reaction mixture was filtered and concentrated in vacuo to give a solid that was recrystallised from a mixture of isohexane and EtOAc (10:1) to give the title compound (2.2 g, 32%) as a solid; 1H NMR δ (CDCl3) 1.0-1.3 (2H, m), 1.08 (3H, d), 1.2 (3H, t), 1.3-1.45 (2H, m), 1.45-1.64 (2H, m), 1.65-1.75 (1H, m), 1.77-1.9 (3H, m), 2.15-2.26 (1H, m), 2.28-2.39 (1H, m), 4.1 (2H, q), 6.68 (2H, d), 7.0 (2H, d).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customto give a solid
  4. customthat was recrystallised from a mixture of isohexane and EtOAc (10:1)

Sources & evidence

ORD record
ord-af82f621d7b14cee987d91d70312d835
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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