HCID 69870925, compound → HCID 22633482, compound

HRID 398177Notes

Reaction equation

HRID 398177 reaction equation
C([O:3][C:4](=[O:29])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]CC2C=CC=CC=2)=[CH:11][C:10]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:7])[CH3:6])C.[H][H]>C(O)C.[Pd]>[OH:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:5]([CH3:7])([CH3:6])[C:4]([OH:29])=[O:3])=[C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:11]=1

Participants

5

Reactant 2

HCID 69870925HCID 69870925, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22633482HCID 22633482, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(5-benzyloxy-biphenyl-2-yloxy)-2-methyl-propionic acid ethyl ester (3.58 g, 7.63 mmol maximum) in ethanol (75 mL) was treated with 5% Pd/C (3.0 g) and hydrogen (balloon, room temperature, 16 h). The mixture was filtered and concentrated to a viscous colorless oil (2.44 g, 107%): 1H NMR (400 MHz, CDCl3) δ1.25 (t, 3H, J=7.1 Hz), 1.27 (s, 6H), 4.20 (q, 2H, J=7.3 Hz), 4.95 (brs, 1H), 6.67 (dd, 1H, J=3.4, 8.8 Hz), 6.81 (d, 1H, J=3.4 Hz), 6.88 (d, 1H, J=8.8 Hz), 7.30 (dt, 1H, J=1.5, 7.3 Hz), 7.37 (dt, 2H, J=1.5, 7.3 Hz), 7.52 (dd, 2H, J=1.5, 6.8Hz).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated to a viscous colorless oil (2.44 g, 107%)

Sources & evidence

ORD record
ord-250175d78e274e8c8f3f5c563921c16e
Source dataset
uspto-grants-2003_08
Patent number
US06610696B2

Reaction notes

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