Sodium Hydroxide → HCID 15337400, compound

HRID 441152Notes

Reaction equation

HRID 441152 reaction equation
Br[C:2]1[O:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=1.[C:19]1(OB(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Na+].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:18][S:17][C:14]1[CH:15]=[CH:16][C:11]([C:3]2[C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[O:6][C:2]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 78412Phenyl dihydrogen orthoborateHCID 516892Sodium BicarbonateHCID 18347198HCID 18347198, compound

Product 1

HCID 15337400HCID 15337400, compoundYield 67.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of the product of Step 3 (450 mg), phenylboric acid (750 mg), Pd (PPh3)4 (80 mg) and NaOH (3 mL, 1N) in toluene (8 ml) and EtOH (10 mL) was refluxed for 20 h. A saturated solution of NaHCO3 (50 ml) was added and the mixture was extracted with Et2O (200 mL). The extract was dried over MgSO4 and concentrated. The residue was purified by flash chromatography eluted with 30:1 hexane/EtOAc to give the title compound (300 mg).

Workup

  1. temperaturewas refluxed for 20 h
  2. extractionthe mixture was extracted with Et2O (200 mL)
  3. dry with materialThe extract was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluted with 30:1 hexane/EtOAc

Sources & evidence

ORD record
ord-3521f16cd8b64dc494a42e41219da601
Source dataset
uspto-grants-1996_05
Patent number
US05521213

Reaction notes

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