Ammonium Chloride → HCID 86599463, compound

HRID 854910Notes

Reaction equation

HRID 854910 reaction equation
[F:1][C:2]([F:30])([F:29])[O:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([C:14]#[C:15][Si](C)(C)C)[CH:13]=1)[O:10][CH:9]([C:20]([F:23])([F:22])[F:21])[C:8]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:7]2.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[NH4+].[Cl-]>C(Cl)Cl>[C:14]([C:12]1[CH:13]=[C:4]([O:3][C:2]([F:30])([F:1])[F:29])[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:20]([F:23])([F:22])[F:21])[C:8]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:7]2)#[CH:15]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 86599461HCID 86599461, compound

Product 1

HCID 86599463HCID 86599463, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 6-(trifluoromethoxy)-2-(trifluoromethyl)-8-[(trimethylsilyl)ethynyl]-2H-chromene-3-carboxylate prepared as in Step 1 (22.8 g, 50.3 mmole) in anhydrous CH2Cl2 (200 mL) was added a solution of TBAF (62.9 mL-1.0 M in THF), 62.9 mmole) under a dry N2 atmosphere. The mixture was stirred for 10 minutes and then poured into sat. NH4Cl (200 mL) and extracted with EtOAc (500 mL). The EtOAc extract was washed with brine (100 mL), dried over MgSO4, filtered and concentrated in vacuo to give 40 g of a dark brown oil. The crude product was purified by silica chromatography (98:2 hexanes:CH2Cl2) to give 13.9 g (73% yield) of the product as a yellow crystalline solid: EIHRMS m/z 380.0505 (M+, C16H10F6O4, Calc'd 380.0483).

Workup

  1. extractionextracted with EtOAc (500 mL)
  2. extractionThe EtOAc extract
  3. washwas washed with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd991137409c4980a50c364204fe7798
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

Loading…