HCID 69469338, compound → HCID 22280115, compound

HRID 1063679Notes

Reaction equation

HRID 1063679 reaction equation
[CH3:1][C:2]1[CH:12]=[C:11]([CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]>O1CCCC1.[Pd]>[CH3:1][C:2]1[CH:12]=[C:11]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

4

Reactant 1

HCID 69469338HCID 69469338, compound

Product 1

HCID 22280115HCID 22280115, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of {2-methyl-4-[2-(4′-trifluoromethyl-biphenyl-4-yl)-vinyl]-phenoxy}-acetic acid (0.98 g, 2.4 mmol) in 100 ml of tetrahydrofuran was hydrogenated over 0.16 g of 20% palladium on carbon catalyst. The catalyst was removed by filtration, and the filtrate was evaporated. The crude product was recrystallized from aqueous acetonitrile. mp 174-176° C.; IR (thin film) cm−1: 1747, 1711, 1500, 1318, 1160, 1123; 400 MHz 1H NMR (DMSO-d6) δ 7.83 (d, 2H, J=8.1 Hz), 7.74 (d, 2H, J=8.3 Hz), 7.60 (d, 2H, J=6.5 Hz), 7.32 (d, 2H, J=8.3 Hz), 7.01 (d, 1H, J=2.0 Hz), 6.94 (dd, 1H, J=2.0, 8.3 Hz), 6.66 (d, 1H, J=8.3 Hz), 4.59 (s, 2H), 2.83 (m, 2H), 2.76 (m, 2H), 2.11 (s, 3H); MS m/z 413 (M−1). Anal. Calc'd for C24H21F3O3: C, 69.56; H, 5.11. found: C, 69.28; H, 4.96.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. customThe crude product was recrystallized from aqueous acetonitrile

Sources & evidence

ORD record
ord-7b3896b6905b4b8393e4d46dad0997e1
Source dataset
uspto-grants-2005_11
Patent number
US06964983B2

Reaction notes

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