Cesium fluoride → HCID 18687737, compound

HRID 1872872Notes

Reaction equation

HRID 1872872 reaction equation
[F:1][C:2]1[C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:7][C:6]=2[C:5]([Si](C)(C)C)=[C:4]([O:20][CH:21]([CH3:23])[CH3:22])[CH:3]=1.[F-].[Cs+]>CN(C=O)C.[Cl-].[Na+].O>[F:1][C:2]1[C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:7][C:6]=2[CH:5]=[C:4]([O:20][CH:21]([CH3:23])[CH3:22])[CH:3]=1

Participants

5

Reactant 2

HCID 25953Cesium fluorideHCID 18687721HCID 18687721, compound

Product 1

HCID 18687737HCID 18687737, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A stirred solution of 1-fluoro-3-isopropoxy-4-(trimethylsilyl)phenoxathiin (230 mg, 0.66 mmol) (Example 25) and CsF (200 mg, 1.32 mmol) in 5 mL 10% (v/v) aqueous DMF was heated under nitrogen at 100° C. for 0.5 h. After cooling to room temperature, the reaction was diluted with brine (30 mL), dried (Na2SO4), and concentrated in vacuo to a pale yellow oil (178 mg). Filtration of the crude product through silica gel (20 g) with 10% CH2Cl2 /hexanes yielded 142 mg (78%) of the title compound as a colorless oil: TLC (CH2Cl2 /hexanes, 10:90) Rf =0.31; 1H-NMR (CDCl3) d, J=6 Hz, 6 H), 4.43-4.47 (m, 1 H), d 6.36-6.41 (m, 2 H), C2 --H and C4 -H), d 6.95-7.14 (m, 4 H); MS m/e (relative intensity) 277 (MH+, 100).

Workup

  1. dry with materialdried (Na2SO4)
  2. concentrationconcentrated in vacuo to a pale yellow oil (178 mg)
  3. filtrationFiltration of the crude product through silica gel (20 g) with 10% CH2Cl2 /hexanes

Sources & evidence

ORD record
ord-cb9bc995985e4be3b413834662050a55
Source dataset
uspto-grants-2000_08
Patent number
US06110961

Reaction notes

Loading…