Triphenylphosphine → HCID 18374456, compound

HRID 1018954Notes

Reaction equation

HRID 1018954 reaction equation
I[C:2]1[CH:3]=[C:4]([P:8](=[O:15])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])[CH:5]=[CH:6][CH:7]=1.[OH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.CCOC(C)=O>[CH2:10]([O:9][P:8]([C:4]1[CH:3]=[C:2]([C:21]2[CH:22]=[CH:23][C:18]([CH2:17][OH:16])=[CH:19][CH:20]=2)[CH:7]=[CH:6][CH:5]=1)(=[O:15])[O:12][CH2:13][CH3:14])[CH3:11]

Participants

8

Reactant 3

HCID 11776TriphenylphosphineHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 18374549HCID 18374549, compound

Product 1

HCID 18374456HCID 18374456, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the product of Step 1 (680 mg, 2 mmol) in toluene (10 mL)—H2O (3 mL)—n Propanol (3 mL) were added 4-hydroxymethyl phenyl boronic acid (607 mg, 4 mmol), tris(dibenzylidene acetone)dipalladium (92 mg, 0.1 mmol), triphenylphosphine (209 mg, 0.8 mmol) and EtNH (175 mg, 2.4 mmol). After a period of 18 h at 90° C., the reaction mixture was partionned between EtOAc and H2O. The organic phase was separated, dried over NaSO4, filtered and evaporated under reduced pressure. The title compound was obtained after flash chromatography (446 mg, 69%).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over NaSO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-de7aee43d0b641aeaa36b43cb33eac2b
Source dataset
uspto-grants-2002_11
Patent number
US06486141B2

Reaction notes

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