Cesium carbonate → 3-[4-(Tert-butyldiphenylsilanyloxy)-2-(4-trifluoromethylphenoxymethyl)phenyl]propionic acid tert-butyl ester

HRID 1181125Notes

Reaction equation

HRID 1181125 reaction equation
[C:1]([O:5][C:6](=[O:35])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[CH2:33]Br)([CH3:4])([CH3:3])[CH3:2].[F:36][C:37]([F:46])([F:45])[C:38]1[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:35])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[CH2:33][O:44][C:41]1[CH:42]=[CH:43][C:38]([C:37]([F:36])([F:45])[F:46])=[CH:39][CH:40]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 678744-(Trifluoromethyl)phenolHCID 589793453-[2-Bromomethyl-4-(tert-butyldiphenylsilanyloxy)phenyl]propionic acid tert-butyl ester

Product 1

HCID 589792643-[4-(Tert-butyldiphenylsilanyloxy)-2-(4-trifluoromethylphenoxymethyl)phenyl]propionic acid tert-butyl esterYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 50 mL round bottomed flask was charged with 3-[2-bromomethyl-4-(tert-butyldiphenylsilanyloxy)phenyl]propionic acid tert-butyl ester (1.0 g, 1.81 mmol), anhydrous DMF (10 mL), and then 4-trifluoromethylphenol (0.44 g, 2.7 mmol) and cesium carbonate (0.88 g, 2.7 mmol). The reaction mixture was stirred at ambient temperature under a nitrogen atmosphere for 18 h and concentrated. The residue was diluted with EtOAc (100 mL). The organic layer was washed with brine (2×), dried (Na2SO4), and concentrated to a yellow oil. The crude residue was purified using radial (EtOAc:hexanes 15:85 to 50:50) to give a yellow oil (0.66 g, 58%). MS (ES) m/e 635 (M+1).

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with EtOAc (100 mL)
  3. washThe organic layer was washed with brine (2×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to a yellow oil
  6. customThe crude residue was purified

Sources & evidence

ORD record
ord-35299251b79a42b6af60f077f1341372
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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