Potassium Phosphate, Tribasic → HCID 89451937, compound

HRID 1497497Notes

Reaction equation

HRID 1497497 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[CH:5]=[CH:4][C:3]=1[CH2:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P([CH:48]2[CH2:53][CH2:52]CCC2)C2CCCCC2)CCCCC1.C1(B(O)O)CC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Si:9]([O:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[C:2]([CH:52]2[CH2:53][CH2:48]2)[CH:7]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 131734205HCID 131734205, compound

Product 1

HCID 89451937HCID 89451937, compoundYield 230.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of benzyl (2-bromo-4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)acetate (250 mg) in toluene (5.00 mL) were added water (0.250 mL), potassium phosphate (366 mg), tricyclohexylphosphine (64.4 mg), palladium (II) acetate (25.8 mg), and cyclopropylboronic acid (98.6 mg), followed by stirring at 110° C. overnight. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution in this order, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain benzyl (4-{[tert-butyl(dimethyl)silyl]oxy}-2-cyclopropylphenyl)acetate (210 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution in this order, then dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-dd3f522e814849c791c0a2e4df280ac0
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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