Triphenylphosphine → HCID 22406566, compound

HRID 440279Notes

Reaction equation

HRID 440279 reaction equation
[C:1]([O:5][C:6]([C:8]1[S:12][C:11]([NH:13]C(OCC=C)=O)=[C:10]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC1(C)CC(=O)CC(=O)C1>C1COCC1.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>[C:1]([O:5][C:6]([C:8]1[S:12][C:11]([NH2:13])=[C:10]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 31358DimedoneHCID 22406552HCID 22406552, compound

Product 1

HCID 22406566HCID 22406566, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl-2-allyloxycarbonylamino-3-tertbutoxy-5-thiophenecarboxylate (1.64 g, 4.62 mmol) in anhydrous THF (50 ml) was treated with PPh3 (240 mg, 0.923 mmol), dimedone (1.3 g, 9.23 mmol) and Pd(PPh3)4 (300 mg, 0.277 mmol). After 30 minutes, the solvent was evaporated, and the residue purified by flash silica-gel chromatography, eluting with petroleum ether: ether (80:20), to give the title compound (975 mg, 98%).

Workup

  1. customthe solvent was evaporated
  2. customthe residue purified by flash silica-gel chromatography
  3. washeluting with petroleum ether: ether (80:20)

Sources & evidence

ORD record
ord-8c2b2c3dd61943f0ae7f8e468426493c
Source dataset
uspto-grants-1996_05
Patent number
US05519015

Reaction notes

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