Acetic Acid → HCID 135416033, compound

HRID 860676Notes

Reaction equation

HRID 860676 reaction equation
[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]([C:15]2[O:19][C:18]([C:20]3[CH:25]=[CH:24][C:23](B4OC(C)(C)C(C)(C)O4)=[CH:22][CH:21]=3)=[N:17][C:16]=2[CH:35]([CH3:37])[CH3:36])[CH3:14])=[CH:8][C:7]=1[CH3:38].CC(O)=[O:42].OO.[O-]S([O-])(=S)=O.[Na+].[Na+]>C1COCC1.O>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]([C:15]2[O:19][C:18]([C:20]3[CH:21]=[CH:22][C:23]([OH:42])=[CH:24][CH:25]=3)=[N:17][C:16]=2[CH:35]([CH3:37])[CH3:36])[CH3:14])=[CH:8][C:7]=1[CH3:38]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 24477Sodium ThiosulfateHCID 58765711HCID 58765711, compound

Product 1

HCID 135416033HCID 135416033, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[4-(1-{4-Isopropyl-2-[4-(4,4,5,5-tetramethyl [1,3,2]dioxaborolan-2-yl)-phenyl]-oxazol-5-yl}-ethoxy)-2-methyl-phenyl]-propionic acid methyl ester (0.88 g, 1.69 mmol) in THF (5 ml) at 0° C. is treated with HOAc (150 mg, 2.54 mmol), followed by addition of mixture of H2O2 (4.0 ml, 30%) in H2O (0.8 ml). The reaction mixture is stirred for 2 hours while warmed to room temperature. The mixture is then cooled back to 0° C. and treated with saturated aqueous Na2S2O3 (30 ml) carefully. The mixture is then extracted with EtOAc (3×100 mL) and the combined organics are dried over Na2SO4 and concentrated, purified by silica gel chromatography (Hexanes/EtOAc, 7/3 to 5/5) to afford the phenol as a colorless oil (0.62 g, 87%). MS (MH+): 424.4.

Workup

  1. temperatureThe mixture is then cooled back to 0° C.
  2. extractionThe mixture is then extracted with EtOAc (3×100 mL)
  3. dry with materialthe combined organics are dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (Hexanes/EtOAc, 7/3 to 5/5)

Sources & evidence

ORD record
ord-0d4af07fbcd846218de57f23aefbed77
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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