HCID 86596231, compound → HCID 68867534, compound

HRID 1985266Notes

Reaction equation

HRID 1985266 reaction equation
[CH2:1]([O:3][C:4](=[O:40])[C:5]([CH3:39])([O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=1)[CH:6]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20]CC2C=CC=CC=2)[CH:15]=1)OC(=O)C(F)(F)F)[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:40])[C:5]([CH3:39])([O:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]([F:37])([F:38])[F:36])=[CH:33][CH:34]=1)[CH2:6][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=1)[CH3:2]

Participants

4

Reactant 1

HCID 86596231HCID 86596231, compound

Product 1

HCID 68867534HCID 68867534, compoundYield 33.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The 3-(3-benzyloxy-phenyl)-2-methyl-3-(2,2,2-trifluoro-acetoxy)-2-(4-trifluoromethyl-phenoxy)-propionic acid ethyl ester (9.03 g, 15.8 mmol) was combined with 10% Pd/C (9.0 g) in ethyl acetate (200 mL). The mixture was purged with N2 then H2 and then stirred at room temperature under a H2 balloon for approximately 48 h. The reaction mixture was filtered through hyflo to remove the catalyst and the resultant filtrate dried (MgSO4). The solvent was removed in vacuo to give crude product that was purified by flash chromatography using 3:1 hexanes:acetone to afford 1.96 g (32%) 3-(3-hydroxy-phenyl)-2-methyl-2-(4-trifluoromethyl-phenoxy)-propionic acid ethyl ester. The racemic phenol was purified by preparative chiral HPLC (Chiralcel OD, 5×37 cm, 95:5 heptane:IPA mobile phase, 150 ml/min, 285 nm, GK8-A015150-031). Rf=0.32 (1:1 hexanes:acetone). 1 NMR. MS (ES−) Calc'd for C19H18O4F3 (M−1) 367. Found m/z 367 (100%).

Workup

  1. customThe mixture was purged with N2
  2. filtrationThe reaction mixture was filtered through hyflo
  3. customto remove the catalyst
  4. dry with materialthe resultant filtrate dried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. customto give crude product that
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-dcca5d7e418848cf80d8037a10e5d87c
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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