1,3-Bis(diphenylphosphino)propane → HCID 131722865, compound

HRID 1596872Notes

Reaction equation

HRID 1596872 reaction equation
[CH2:1]([O:3]C(=O)C1C=CC(C#CC2C=CC3C(N(C4CC4)C)CCC(C)(C)C=3C=2)=CC=1F)C.C([O:35][C:36]1[CH:41]=[CH:40][C:39](O)=[CH:38][C:37]=1[C:43]([CH3:46])([CH3:45])[CH3:44])(=O)C.[C:47]([O:51][C:52](=[O:61])[CH2:53][C:54]1[CH:59]=[CH:58][C:57]([OH:60])=[CH:56][CH:55]=1)([CH3:50])([CH3:49])[CH3:48].[C:62]1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:63]=1>CS(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C.ClCCCl>[C:47]([O:51][C:52]([CH2:53][C:54]1[CH:55]=[CH:56][C:57]([O:60][C:1]([CH:41]2[CH:40]=[CH:39][C:38]3[CH2:63][CH2:62][CH2:46][C:43]([CH3:44])([CH3:45])[C:37]=3[C:36]2=[O:35])=[O:3])=[CH:58][CH:59]=1)=[O:61])([CH3:50])([CH3:48])[CH3:49]

Participants

9

Reactant 4

HCID 812191,3-Bis(diphenylphosphino)propaneHCID 15932404Tert-butyl 2-(4-hydroxyphenyl)acetateHCID 23442872t-Butyl-4-hydroxy-phenyl acetateHCID 69548663HCID 69548663, compound2×

Product 1

HCID 131722865HCID 131722865, compoundYield 53%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 111,2-DichloroethaneSolventHCID 679Dimethyl SulfoxideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 4,4-dimethyl-6-trifluoromethylsulfonyloxy-1,2,3,4-tetrahydronaphthalene-1-one (Intermediate 11, 0.14 g, 0.434 mmol), t-butyl-4-hydroxy-phenyl acetate (Reagent E, 0.14 g, 0.673 mmol), palladium acetate (0.054 g, 0.24 mmol) and 1,3-bis(diphenylphosphino)propane (0.082 g, 0.2 mmol) in a mixture of dimethylsulfoxide (1 mL), 1,2-dichloroethane (1.5 mL) and triethyl amine (1 mL) was heated at 70° C. under an atmosphere of carbon monoxide overnight. The volatiles were distilled of in vacuo and the residue was diluted with water and extracted with diethyl ether (×3). The combined organic extract was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to an oil which was subjected to flash column chromatography over silica gel (230-400 mesh) using 15% ethyl acetate in hexane as the eluent to afford the title compound (0.11 g, 53%).

Workup

  1. distillationThe volatiles were distilled of in vacuo
  2. additionthe residue was diluted with water
  3. extractionextracted with diethyl ether (×3)
  4. extractionThe combined organic extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to an oil which

Sources & evidence

ORD record
ord-d76874e5224d47ad9c482dd36eae9571
Source dataset
uspto-grants-2001_09
Patent number
US06291677B1

Reaction notes

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