Triphenylphosphine → HCID 19744806, compound

HRID 2254484Notes

Reaction equation

HRID 2254484 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:11]=O)[S:9][CH:10]=2)=[CH:2]1.[Cl-].[Cl:14][CH2:15][C:16]1[CH:17]=[C:18]([CH:39]=[CH:40][CH:41]=1)[CH2:19][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.ClCC1C=CC=C(CCl)C=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[H-].[Na+]>O1CCCC1.C1(C)C(C)=CC=CC=1>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8](/[CH:11]=[CH:19]/[C:18]3[CH:17]=[C:16]([CH:41]=[CH:40][CH:39]=3)[CH2:15][Cl:14])[S:9][CH:10]=2)=[CH:2]1

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 12275Benzene, 1,3-bis(chloromethyl)-HCID 24758Sodium hydrideHCID 16218061[3,3'-Bithiophene]-5-carbaldehydeHCID 19744545HCID 19744545, compound

Product 1

HCID 19744806HCID 19744806, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8028TetrahydrofuranSolvent

Procedure

100 mg of 4-(3-thienyl)-2-thiophenecarboxaldehyde and 250 mg of 3-chloromethylbenzyltriphenylphosphonium chloride [prepared by refluxing a xylene solution of α,α'-dichloro-m-xylene and triphenylphosphine] were suspended in 1 ml of tetrahydrofuran, and 31 mg of 60% oily sodium hydride was added under ice cooling. The mixture was stirred for 1.5 hours at room temperature, and the solvent was evaporated. The residue was neutralized with 1 N HCl, and extracted with ethyl acetate. The extract was worked up in a customary manner, purified by silica gel column chromatography [Wakogel C-300, 5 g; eluting solvent: hexane/ethyl acetate=10/1], and recrystallized from chloroform-hexane to give 80 mg (yield 49%) of the captioned compound as a pale yellow crystalline powder, m.p. 137°-138° C.

Workup

  1. customthe solvent was evaporated
  2. extractionextracted with ethyl acetate
  3. custompurified by silica gel column chromatography [Wakogel C-300, 5 g; eluting solvent: hexane/ethyl acetate=10/1]
  4. customrecrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-257dc4e5a8fc4dedb3d0c5fdfeababb9
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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