Pyridine → HCID 21619938, compound

HRID 2225917Notes

Reaction equation

HRID 2225917 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3](=[O:13])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[P:16](Cl)([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17].N1C=CC=CC=1.ClCCl>CCCCCC.C(OCC)(=O)C>[P:16]([O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3](=[O:13])[C:2]([F:14])([F:15])[F:1])=[CH:7][CH:8]=1)([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 13139Diethyl chlorophosphateHCID 1952441,1,1-Trifluoro-4-(4-hydroxyphenyl)butan-2-one

Product 1

HCID 21619938HCID 21619938, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 10 mL one neck round bottom flask, fitted with argon inlet and magnetic stirrer was placed in an ice bath and charged with 400 mg(1.8 mM) of 1,1,1-trifluoro-4-(4-hydroxyphenyl)-2-butanone, 400 mg(2.4 mM) of diethyl chlorophosphate, 0.15 mL of dry pyridine and 5 mL of dichloromethane at 5° C. The mixture was stirred overnight at ambient temperature, filtered to remove pyridine HCl, extracted with 0.2N HCl, extracted with water, and dried (anhydrous MgSO4). Solvent removal under reduced pressure gave a crude yield of 600 mg of a brown oil. Preparative TLC using 1:1 ethyl acetate:hexane gave 600 mg(92%) of a clear oil nmr(CDCl3) - L 1.50(m,6H), 3.0(m,4H), 4.20(m,4H), 7.15(s,4H).

Workup

  1. customwas placed in an ice bath
  2. filtrationfiltered
  3. customto remove pyridine HCl
  4. extractionextracted with 0.2N HCl
  5. extractionextracted with water
  6. dry with materialdried (anhydrous MgSO4)
  7. customSolvent removal under reduced pressure
  8. customgave a crude yield of 600 mg of a brown oil

Sources & evidence

ORD record
ord-4a17749cb3c84f11b8d0fe3be4d3f08d
Source dataset
uspto-grants-1994_09
Patent number
US05344952

Reaction notes

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