Triphenylphosphine → HCID 21831301, compound

HRID 977617Notes

Reaction equation

HRID 977617 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH2:14][F:15])([CH2:12][F:13])[CH:9]=[C:8](OS(C(F)(F)F)(=O)=O)[C:7]=2[CH:24]=1)#[N:2].C[Sn](C)(C)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Li+]>CCOCC.O1CCCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH2:12][F:13])([CH2:14][F:15])[CH:9]=[C:8]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[C:7]=2[CH:24]=1)#[N:2]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 11021057Pyridine, 2-(trimethylstannyl)-HCID 21831356HCID 21831356, compound

Product 1

HCID 21831301HCID 21831301, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 120 mg of 6-cyano-4-trifluoromethanesulfonyloxy-2,2-bisfluoromethyl-2H-1-benzopyran, 87 mg of 2-trimethylstannylpyridine, 25.4 mg of tris-dibenzylidene acetone chloroform dipalladium (0), 12.8 mg of triphenylphosphine, 110 mg of lithium chloride and 6 ml of dry tetrahydrofuran was refluxed for 6.5 hours. After cooling, ether was added and the mixture was filtered using Celite. After the organic layer of the mother liquor was washed with water and dried, the solvent was distilled off. The resultant residue was purified using silica gel column chromatography (developing solution, CH2Cl2) to obtain 80 mg of oily 6-cyano-2,2-bisfluoromethyl-4-(2-pyridyl)-2H-1-benzopyran represented by the following formula.

Workup

  1. temperaturewas refluxed for 6.5 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. washAfter the organic layer of the mother liquor was washed with water
  5. customdried
  6. distillationthe solvent was distilled off
  7. customThe resultant residue was purified

Sources & evidence

ORD record
ord-62e8f7e6b83946bb954b89ffdcf406e1
Source dataset
uspto-grants-1997_03
Patent number
US05614633

Reaction notes

Loading…