Triphenylphosphine → HCID 100991458, compound

HRID 1422468Notes

Reaction equation

HRID 1422468 reaction equation
Br[C:2]1[S:3][C:4]([Sn](C)(C)C)=[CH:5][C:6]=1[CH2:7][CH2:8][C:9]1[O:10][CH2:11][C:12]([CH3:15])([CH3:14])[N:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cu]=O.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].CN(C=O)C>[CH3:14][C:12]1([CH3:15])[CH2:11][O:10][C:9]([CH2:8][CH2:7][C:6]2[CH:5]=[CH:4][S:3][CH:2]=2)=[N:13]1

Participants

6

Reactant 2

HCID 11776TriphenylphosphineHCID 69249597HCID 69249597, compound

Product 1

HCID 100991458HCID 100991458, compound

Reagents, catalysts & solvents 3

HCID 14829Copper oxideCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2-(2-(2-bromo-5-(trimethylstannyl)thiophen-3-yl)ethyl)-4,5-dihydro-4,4-dimethyloxazol (7.0 g, 15.5 mmol) was weighed in 100 mL Schlenk flask followed by the addition of 30 mL dry DMF then purged with nitrogen for 15 min. To this mixture, copper (II) oxide (1.24 g, 15.5 mmol, 1 eq.), triphenylphosphine (814 mg, 0.031 mmol, 0.20 eq.) and bis(dibenzylidene acetone)palladium(0) (446 mg, 0.776 mmol, 0.05 eq) was added all at once. The greenish-brown suspension solution was purged with nitrogen for 15 min then heated to 100° C. and stirred for 18 hrs under argon atmosphere. The reaction mixture was filtered thru celite and the purple precipitate was extracted with chloroform. The chloroform extract was concentrated and the resulting solid was soxhlet-extracted with hexanes then extracted with chloroform. The solvent was removed to afford a purple solid (2.1 g, 66% S5 yield). 1H NMR (300 MHz, CDCl3): δ=7.06 (s, 1H), 3.94 (s, 2H), 3.14 (d, 2H), 2.66 (d, 2H), 1.28 (s, 6H); 13C NMR (75 MHz, CDCl3): δ=166.7, 138.4, 134.4, 132.4, 129.8, 80.0, 68.0, 29.6, 29.2, 26.4. CDCl3

Workup

  1. customthen purged with nitrogen for 15 min
  2. customThe greenish-brown suspension solution was purged with nitrogen for 15 min
  3. filtrationThe reaction mixture was filtered thru celite
  4. extractionthe purple precipitate was extracted with chloroform
  5. extractionThe chloroform extract
  6. concentrationwas concentrated
  7. extractionthe resulting solid was soxhlet-extracted with hexanes
  8. extractionthen extracted with chloroform
  9. customThe solvent was removed
  10. customto afford
  11. customa purple solid (2.1 g, 66% S5 yield)

Sources & evidence

ORD record
ord-c89b4e1f616345c2bd9baf2e774fdfab
Source dataset
uspto-grants-2015_01
Patent number
US08927293B2

Reaction notes

Loading…