Sodium Iodide → HCID 86622682, compound

HRID 1694670Notes

Reaction equation

HRID 1694670 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:33]([F:36])([F:35])[F:34])[CH:5]=[C:6]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][O:14][C:15]3[CH:24]=[C:23]4[C:18]([C:19](=[O:32])[C:20]([C:25]5[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=5)=[CH:21][O:22]4)=[CH:17][CH:16]=3)[N:12]=2)[CH:7]=1.[P:37]([O:49][CH2:50]Cl)([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38].CC(C)([O-])C.[K+].[I-].[Na+]>CN(C)C=O.O>[P:37]([O:49][CH2:50][O:31][C:28]1[CH:27]=[CH:26][C:25]([C:20]2[C:19](=[O:32])[C:18]3[C:23](=[CH:24][C:15]([O:14][CH2:13][C:11]4[N:12]=[C:8]([C:6]5[CH:7]=[C:2]([F:1])[CH:3]=[C:4]([C:33]([F:34])([F:36])[F:35])[CH:5]=5)[O:9][CH:10]=4)=[CH:16][CH:17]=3)[O:22][CH:21]=2)=[CH:30][CH:29]=1)([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])([O:44][C:45]([CH3:46])([CH3:47])[CH3:48])=[O:38]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11701630Di-tert-butyl (chloromethyl) phosphateHCID 23665647Potassium tert-butoxideHCID 42605467HCID 42605467, compound

Product 1

HCID 86622682HCID 86622682, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a 50 mL round bottomed flask 7-({2-[5-fluoro-3-(trifluoromethyl)phenyl](1,3-oxazol-4-yl)}methoxy)-3-(4-hydroxyphenyl)chromen-4-one (150.0 mg, 0.302 mmol) was treated with di-tert-butyl chloromethyl phosphate (156.2 mg, 0.604 mmol, 1.0 equiv) in the presence of potassium t-butoxide (67.8 mg, 0.604 mmol, 1.0 equiv) and sodium iodide (89.9 mg, 0.604 mmol, 1.0 equiv) in N,N-dimethylformamide (2 ml), and the mixture stirred at room temperature for 15 hours. To the mixture was added water (30 ml), and the whole was extracted with ethyl acetate (30 ml×3). The combined organic layers were washed with brine (30 ml), dried with Na2SO4, and solvent removed under reduced pressure, to give a crude mixture (345.1 mg). This mixture was purified by column-chromatography (SiO2=80 g, hexane/EtOAc=1:1) to give di-tert-butyl {4-[7-({2-[5-fluoro-3-(trifluoromethyl)phenyl](1,3-oxazol-4-yl)}methoxy)-4-oxochromen-3-yl]phenoxy}methyl phosphate as a colorless oil.

Workup

  1. extractionthe whole was extracted with ethyl acetate (30 ml×3)
  2. washThe combined organic layers were washed with brine (30 ml)
  3. dry with materialdried with Na2SO4, and solvent
  4. customremoved under reduced pressure
  5. customto give a crude mixture (345.1 mg)
  6. customThis mixture was purified by column-chromatography (SiO2=80 g, hexane/EtOAc=1:1)

Sources & evidence

ORD record
ord-8b79ea6139b147abb8579266cf7c353b
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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