Triphenylphosphine → HCID 66671487, compound

HRID 902598Notes

Reaction equation

HRID 902598 reaction equation
I[CH2:2][C:3]([O:5][CH:6]=[CH2:7])=[O:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[H-].[Na+].[C:29]1([N:35]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:36]2[CH:43]=[CH:42][C:39]([CH:40]=O)=[CH:38][CH:37]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1.C(OCC)C>[CH:6]([O:5][C:3](=[O:4])[CH:2]=[CH:40][C:39]1[CH:38]=[CH:37][C:36]([N:35]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:43][CH:42]=1)=[CH2:7]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 24758Sodium hydrideHCID 77846Benzaldehyde, 4-(diphenylamino)-HCID 21681881Ethenyl iodoacetate

Product 1

HCID 66671487HCID 66671487, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
6 °C

Procedure

A 100 mL round bottom flask equipped with a nitrogen inlet-outlet, magnetic stirrer and addition funnel was charged with vinyl iodoacetate (5.6 g, 26 mmol) and triphenylphosphine (6.9 g, 26 mmol) in 50 mL anhydrous tetrahydrofuran. The reaction mixture was blanketed with nitrogen and allowed to stir for 16 h and then cooled to 6° C. on an ice-water bath. Sodium hydride (1.0 g, 25 mmol) was added and the reaction was allowed to warm to room temperature. After stirring at room temperature for 4 h, 4-diphenylaminobenzaldehyde (5.4 g, 20 mmol) dissolved in 40 mL anhydrous THF was added dropwise to the stirring reaction mixture over 30 minutes. After stirring at room temperature for five days, the reaction mixture was diluted with 50 mL diethyl ether and transferred to a separatory funnel. An additional 300 mL diethyl ether was added to the separatory funnel and the combined ether solution was washed three times with 100 mL water and one time with 100 mL saturated NaCl solution. The organic layer was dried over MgSO4, filtered and concentrated on a rotary evaporator. The residue was further dried on a high vacuum line to yield the crude product as a brown oil. After purification by flash column chromatography (silica gel; 3:7 dichloromethane:hexanes) 5.5 g of the pure product was obtained as a light yellow oil. The product yield was 81%.

Workup

  1. customA 100 mL round bottom flask equipped with a nitrogen inlet-outlet, magnetic stirrer and addition funnel
  2. temperatureto warm to room temperature
  3. stirringAfter stirring at room temperature for 4 h
  4. additionwas added dropwise to the stirring reaction mixture over 30 minutes
  5. stirringAfter stirring at room temperature for five days
  6. customtransferred to a separatory funnel
  7. washthe combined ether solution was washed three times with 100 mL water and one time with 100 mL saturated NaCl solution
  8. dry with materialThe organic layer was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated on a rotary evaporator
  11. customThe residue was further dried on a high vacuum line

Sources & evidence

ORD record
ord-ca925d3adebf4526a16f948021cca5b9
Source dataset
uspto-grants-2008_04
Patent number
US07365230B2

Reaction notes

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