Triethylamine → HCID 67058247, compound

HRID 1515096Notes

Reaction equation

HRID 1515096 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)=[CH:15][CH:14]=1)[OH:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:29]1(C2C3C(=C4C(=CC=3)C(C3C=CC=CC=3)=CC=N4)N=CC=2)C=CC=C[CH:30]=1.C(N(CC)CC)C>C(OCCCC)=C.FC(F)(F)C([O-])=O.[Pd+2].FC(F)(F)C([O-])=O>[C:4]([Si:1]([O:8][CH2:9][CH2:10][CH:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)=[CH:15][CH:14]=1)[O:12][CH:29]=[CH2:30])([CH3:3])[CH3:2])([CH3:6])([CH3:7])[CH3:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 728124,7-Diphenyl-1,10-phenanthrolineHCID 67058082HCID 67058082, compound

Product 1

HCID 67058247HCID 67058247, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 2733347Palladium(II) trifluoroacetateCatalystHCID 8108Butyl vinyl etherSolvent

Conditions

Temperature
80 °C

Procedure

3-(tert-Butyldimethylsilyloxy)-1-[4-(3,4-dichlorobenzyloxy)phenyl]propan-1-ol (300 mg, 0.680 mmol) produced in Example 27 (27B), palladium(II) trifluoroacetate (12 mg, 0.036 mmol), and 4,7-diphenyl-1,10-phenanthroline (12 mg, 0.036 mmol) were dissolved in butyl vinyl ether (5 mL), and triethylamine (20 μL, 0.14 mmol) was added thereto, and the resulting mixture was stirred under a nitrogen atmosphere at 80° C. for 4 hours. After cooling to room temperature, the reaction solution was filtered, and the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 96:4 (v/v)), whereby the objective title compound was obtained as a colorless oily substance (275 mg, yield: 87%).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction solution was filtered
  3. distillationthe solvent was distilled off under reduced pressure, whereby a crude product
  4. customwas obtained
  5. customThis crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 96:4 (v/v)), whereby the objective title compound
  6. customwas obtained as a colorless oily substance (275 mg, yield: 87%)

Sources & evidence

ORD record
ord-a75f0e2913b94c80a1078ecde46a78b9
Source dataset
uspto-grants-2012_07
Patent number
US08222281B2

Reaction notes

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